An intermediate compound 2, 4-bis（laurylamino）-6-（1-（2-aminoethyl）-piperazine）-1, 3, 5-triazine was prepared by stepwise nucleophilic substitution on triazine ring by lauryl amine and subsequently 1-（2-aminoet...An intermediate compound 2, 4-bis（laurylamino）-6-（1-（2-aminoethyl）-piperazine）-1, 3, 5-triazine was prepared by stepwise nucleophilic substitution on triazine ring by lauryl amine and subsequently 1-（2-aminoethyl）-piperazine. Then imidization of perylene-3, 4, 9, 10-tetracarboxylic acid dianhydride with 2,4-bis（laurylamino）-6-（1-（2-aminoethyl）-piperazine）-1, 3, 5-triazine was carried out to afford a novel perylene derivative bearing two melamine blocks （S2） and 1, 6, 7, 12-tetra（4-tert-butyl phenoxy）-perylene-3, 4, 9, 10-tetracarboxylic acid bisimide （S1. The hydrogen-bonding interactions between S1 and S2 were investigated by IH NMR spectrum, UV/Vis spectrum and fluorescence spectrum. The influences on the morphologies of S1·S2 aggregates were investigated. The results show that well-defined nanofibers with a diameter of about 100 nm can be obtained by self-assembly between S1 and S2 only in CH2Cl2 solution. Based on these results, guidelines for the molecular design and self-assembly of supramolecular polymer materials are presented.展开更多
Novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores have been prepared conveniently by coupling of 1,8-naphthalimide and dibromoperylene bisimides. Their optical properties were investigate...Novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores have been prepared conveniently by coupling of 1,8-naphthalimide and dibromoperylene bisimides. Their optical properties were investigated by UV-vis and fluorescence spectroscopy. The absorption spectra of these compounds showed wide spectral responses from 300 to 700 nm, which would be potentials for application as organic solar cells.展开更多
A perylene bisimide dye covalently bonded with a hydrogen-bond formation group of 1, 3, 5-triazine-2, 4-diamine has been synthesized. Its casting films show a charge carrier mobility over 10^-3 cm^2/Vs, which is in th...A perylene bisimide dye covalently bonded with a hydrogen-bond formation group of 1, 3, 5-triazine-2, 4-diamine has been synthesized. Its casting films show a charge carrier mobility over 10^-3 cm^2/Vs, which is in the range of the highest values found for other promising charge transport materials suitable for solution processable technique.展开更多
By combining stable radical tetramethylpiperidine nitrogen oxide(TEMPO)as end groups and perylene bisimide(PBI)as the core,a small molecular cathode interlayer(CIL)(PBI-TEMPO)was synthesized.Detailed physical-chemical...By combining stable radical tetramethylpiperidine nitrogen oxide(TEMPO)as end groups and perylene bisimide(PBI)as the core,a small molecular cathode interlayer(CIL)(PBI-TEMPO)was synthesized.Detailed physical-chemical characterizations indicate that PBI-TEMPO can form smooth film,owns low unoccupied molecular orbital(LUMO)level of−3.67 eV and can reduce the work function of silver electrode.When using PBI-TEMPO as CIL in non-fullerene organic solar cells(OSCs),the PM6:BTP-4Cl based OSCs delivered high power conversion efficiencies(PCEs)up to 17.37%,higher than those using commercial PDINO CIL with PCEs of 16.95%.Further device characterizations indicate that PBI-TEMPO can facilitate more efficient exciton dissociation and reduce charge recombination,resulting in enhanced current density and fill factor.Moreover,PBI-TEMPO displays higher thermal stability than PDINO in solution.When PBI-TEMPO and PDINO solution were heated at 150℃ for 2 h and then were used as CIL in solar cells,PBI-TEMPO-based OSCs provided a PCE of 15%,while PDINO-based OSCs only showed a PCE of 10%.These results demonstrate that incorporating TEMPO into conjugated materials is a useful strategy to create new organic semiconductors for application in OSCs.展开更多
Two perylene bisimides based non-fullerene small molecules, H-DIPBI and B-DIPBI, are applied into inverted planar heterojunction perovskite solar cells. The power conversion efficiency up to 11.6% has been achieved fo...Two perylene bisimides based non-fullerene small molecules, H-DIPBI and B-DIPBI, are applied into inverted planar heterojunction perovskite solar cells. The power conversion efficiency up to 11.6% has been achieved for device with B-DIPBI,indicating that non-fullerene acceptor can function as the electron transport layer to replace PCBM in perovskite solar cells.展开更多
Integrating multiple photosensitive properties into an“all-in-one”photosensitizer(PS)shows great promise for the treatment of cancers owing to synergistic effect among them.However,the development of such PSs,especi...Integrating multiple photosensitive properties into an“all-in-one”photosensitizer(PS)shows great promise for the treatment of cancers owing to synergistic effect among them.However,the development of such PSs,especially those that need a single laser source,remains a challenge.Herein,we report an orchestration of electron donors and acceptors in a propeller-like pentad,PBI-4Cz,where four carbazole(Cz)units are covalently linked to the ortho-positions of the perylene bisimide(PBI)core.Strong intramolecular donor-acceptor interaction significantly quenches the luminescence and largely extends the absorption spectra to near-infrared region.Excited-state dynamics investigated via femto-and nano-second transient absorption spectroscopy revealed exclusive charge separation of the PBI-4Cz within initial 0.5 ps when photoexcited regardless of which intermediate is involved.Energy dissipation of the resulting charge-separated state(PBI^(•−)-4Cz^(•−))is subjected to the toggle between intersystem-crossing toward excited triplet states and charge recombination toward ground states.Relative importance of the two pathways can be tuned by micro-environmental polarity,which endows PBI-4Cz remarkable performances of singlet-oxygen generation(>90.0%)in toluene and photothermal conversion(∼28.6%)in DMSO.Harnessing intrinsic photostability and excited-state processes of heavy-atom-free PBI derivatives not only holds a promise for multifunctional phototheranostics,but also provides a prototype for designing high-performance PSs with tunable photoconversion pathways.展开更多
Perylene bisimide （PBI） unit has been widely used to design conjugated materials, which can be used as electron acceptor in organic solar ceils due to its strong electron-deficient ability. In this work, a conjugate...Perylene bisimide （PBI） unit has been widely used to design conjugated materials, which can be used as electron acceptor in organic solar ceils due to its strong electron-deficient ability. In this work, a conjugated polymer based on PBI dimer as monomer was designed, synthesized, and compared to the conjugated polymer containing single PBI as repeating units. The two conjugated polymers were found to have similar molecular weight, absorption spectra and energy levels. Density functional theory calculation revealed that the PBI dimer-based polymer exhibited highly twisted conjugated backbone due to the large dihedral angle between the two PBI units. The PBI-based polymers as electron acceptor were applied into polymer-polymer solar cells, in which PBI dimer-based polymer solar cells were found to show a high short circuit current density （Jsc = 11.2 mA.cm-2） and a high power conversion efficiency （PCE） of 4.5%. In comparison, the solar cells based on PBI-based polymer acceptor only provided a dsc of 7.2 mA.cm-2 and PCE of 2.5%. The significantly enhanced PCE in PBI dimer-based solar cells was attributed to the mixed phase in blended thin films, as revealed by atom force microscopy. This study demonstrates that PB! dimer can be used to design polymer acceptors for high performance polymer- polymer solar cells.展开更多
Designed and synthesized a new highly water soluble N,N^1-bis（2-（（5-（（dimethylamino）methyl）furan-2-yl）methylthio）ethyl）-perylene -3,4,9,10-tetracarboxylic diimide from 2-（（5-（（dimethylamino）methyl）fura...Designed and synthesized a new highly water soluble N,N^1-bis（2-（（5-（（dimethylamino）methyl）furan-2-yl）methylthio）ethyl）-perylene -3,4,9,10-tetracarboxylic diimide from 2-（（5-（（dimethylamino）methyl）furan-2-yl）methylthio）ethanamine and perylene-3,4,9,10- tetracarboxylic dianhydride.The compound was characterized by ~1H,^（13）C,2D NMR,mass and IR techniques.The compound is highly fluorescent with good solubility in water and other polar solvents.展开更多
Neutral perylene bisimides(PBI) are well-known n-type organic semiconductors, with number of challenging electronic properties in their neutral and reduced states. We report the characteristic electronic properties of...Neutral perylene bisimides(PBI) are well-known n-type organic semiconductors, with number of challenging electronic properties in their neutral and reduced states. We report the characteristic electronic properties of PBI anionic films. We unexpectedly discovered that pristine PBI dianion film showed p-type character, while oxidized dianion film(dominant neutral state with few radical anions) showed normal n-type semiconductor character based on Seebeck effect measurements. Both kinds of films exhibit high electrical conductivity with a potential for thermoelectric applications. The mechanism of polarity reversal is proposed.展开更多
In this work, star-shaped perylene bisimide（PBI） derivatives with spiro-aromatic cores linked with ethynyl units were developed as electron acceptors for non-fullerene organic solar cells. The ethynyl linkers were f...In this work, star-shaped perylene bisimide（PBI） derivatives with spiro-aromatic cores linked with ethynyl units were developed as electron acceptors for non-fullerene organic solar cells. The ethynyl linkers were found to enhance the planarity of the conjugated backbone, resulting in high electron mobilities and near-infrared absorption. The ethynyl-linked PBI acceptors showed high power conversion efficiencies（PCEs） up to 4.27% due to the high short-circuit current density（Jsc） of 8.52 mA/cm^2 and fill factor（FF） of 0.59, while the PBI acceptor without ethynyl units provided a low PCE of 3.57% in nonfullerene solar cells. The results demonstrate that ethynyl units can be applied into designing new PBI electron acceptors with improved charge transport properties and photovoltaic performance.展开更多
Rapid and real-time mon itoring of food quality plays critical roles in the food industry and for the gen era I public health.Herei n,we specially synthesized a new perylene bisimide(PBI)derivative(PCB-EpE)composed of...Rapid and real-time mon itoring of food quality plays critical roles in the food industry and for the gen era I public health.Herei n,we specially synthesized a new perylene bisimide(PBI)derivative(PCB-EpE)composed of two PBI units and a rigid o-carborane linker,which was further employed in constructi ng a con ceptual fluoresce nt film sen sor for evaluati ng fish fresh ness.Photophysical studies indicate that PCB-EpE displays an open"Z-type"molecular configuration in chloroform and a closed"△-type"configuration in methyl cyclohexa ne.Comparatively,"Z-type"molecular configurati on possesses higher fluoresce nee qua ntum yield and is more sen sitive toward volatile basic nitrogen(VBN).展开更多
Cathodic electrochromic materials realized by n-type doping of conducting polymers are scarce.Even with limited cases reported in the literature,long-term stability is an urgent problem to be solved.Herein,we report a...Cathodic electrochromic materials realized by n-type doping of conducting polymers are scarce.Even with limited cases reported in the literature,long-term stability is an urgent problem to be solved.Herein,we report a high performance and stable cathodic electrochromic material,poly(Th-Cl-PBI),based on a perylene bisimide function core.Due to its high electropolymerization efficiency and low steric hindrance of thiophene groups,perylene bisimide,which generally does not dissolve and form film easily,can grow to the sufficient thickness of 350 nm for wide-range spectral modulation and large-capacity energy storage.The optical contrast of optimized film with a thickness of 240 nm reaches as high as 69.1% at 520 nm,94.1% at 760 nm,and 95.7% at 680 nm.Theoretical simulation based on the Lambert–Beer law also verifies this optical contrast dependent on film thickness.Besides,during the transition between the neutral state and radical anion state,it maintains 90.2% of the electrochemical activity after 4000 cycles,and the transmittance spectrum remains stable after 2000 cycles.The cation size effect on cathodic electrochromic process and cyclic stability has been investigated.展开更多
We have fabricated a new perylene bisimide(PBI)folda-dimer(BPBI-CB-1)by tethering two PBI moieties to the ortho-carbon positions of a carborane unit.The synthesized compound adopted distinct configurations in differen...We have fabricated a new perylene bisimide(PBI)folda-dimer(BPBI-CB-1)by tethering two PBI moieties to the ortho-carbon positions of a carborane unit.The synthesized compound adopted distinct configurations in different solvents with dual emissions as its characteristic.The two PBI moieties in the molecule appeared either in a weakly interacted,monomer-like state or brought into close π-π contact with each other,forming an interacted stacking state.The equilibrium between these two states was governed by the nature of solvents and testing temperature.Spectroscopic and theoretical studies concluded that dual emission bands originated from intramolecular monomer-like and stacking states,respectively.Remarkably,in a solvent like 1,2-dichloroethane(DCE),both emission intensities increased with rising temperatures.The positive temperature response of the monomer emission was ascribed to an increased amount of monomer-like population,owing to its endothermic energy state,while the excimer emission was rationalized by increased population of the bright exciton state,resulting in an increased emission yield that compensated the diminished population of the stacking state.To our knowledge,this is the first report on positive temperature-responsive dual emissions associated with the synergism of intramolecular intersubunit aggregation/dissociation and excimer transformation.展开更多
Supramolecular polymerization properties have been studied for a series of perylene bisimide(PBI)dyes containing identical hydrogen-bonding amide groups in imide positions but variable number or size of alkoxy substit...Supramolecular polymerization properties have been studied for a series of perylene bisimide(PBI)dyes containing identical hydrogen-bonding amide groups in imide positions but variable number or size of alkoxy substituents in bay-positions.展开更多
Fourfold benzocyclobutene-functionalized perylene bisimide（PBI 4） has been synthesized and its structure was characterized by FTIR,MS and NMR.PBI 4 can react either with itself,or the appropriate dienophiles to form...Fourfold benzocyclobutene-functionalized perylene bisimide（PBI 4） has been synthesized and its structure was characterized by FTIR,MS and NMR.PBI 4 can react either with itself,or the appropriate dienophiles to form the corresponding products under appropriate temperature.The polymer film obtained from the reaction of PBI 4 with methyl vinyl silicone rubber possessed excellent film forming properties including flatness.The optical properties of PBI 4 and polymer film obtained from the reaction of PBI 4 and methyl vinyl silicone rubber have been determined by UV/vis and fluorescence spectroscopy.展开更多
A novel perylene tetracarboxylic acid bisimide（PTCBI） in-chain polyethylene（PE） was first prepared via acyclic diene metathesis（ADMET） polymerization of PTCBI-functionalized α,ω-diene monomer. The polymers cou...A novel perylene tetracarboxylic acid bisimide（PTCBI） in-chain polyethylene（PE） was first prepared via acyclic diene metathesis（ADMET） polymerization of PTCBI-functionalized α,ω-diene monomer. The polymers could spontaneously self-assemble into hollow cylindrical structures in which the π-π interaction between adjacent PTCBI moieties was enhanced and the electron mobility was possibly promoted. The hydrogenation of as-obtained polymer was readily accomplished, affording the desired precision PTCBI in-chain PE with a saturated backbone, which showed high glass transition temperature（Tg = 63 °C）, relatively wide range of light absorption（λ = 200-575 nm）, and higher LUMO level（-3.62 e V）. It can therefore serve as a superior model for facile construction of functional polyolefin and soluble PTCBI polymer with ordered architecture.展开更多
Copper/oxalic diamide-promoted dimerization of tetrachlorinated perylene bisimide to construct highly-fused diperylene bisimides through Ullmann coupling and zipper-mode double C—H activation has been developed in th...Copper/oxalic diamide-promoted dimerization of tetrachlorinated perylene bisimide to construct highly-fused diperylene bisimides through Ullmann coupling and zipper-mode double C—H activation has been developed in this study.This one-step reaction combining homocoupling with C—H activation proceeded smoothly under the action of inexpensive metal-ligand system.This protocol is expected to expand the available synthetic tools for condensed ring systems of perylene bisimide(PBIs).展开更多
An isoindigo-based ＂double-cable＂ conjugated polymer bearing perylene bisimide side units was developed via Stille polymerization for application in single-component polymer solar cells, in which a power conversion ...An isoindigo-based ＂double-cable＂ conjugated polymer bearing perylene bisimide side units was developed via Stille polymerization for application in single-component polymer solar cells, in which a power conversion efficiency of 1% with broad photo-response from 300 nm to 800 nm was achieved. There is no evidence of large phase separation confirmed by AFM images and photoluminescence （PL） spectra. The space charge limit current measurements and light intensity dependence measurements indicate that the low electron mobility and the significant recombination of pho- togenerated charge carriers in active layer mainly account for the low performance of our solar cells. Our results suggest that these ＂double-cable＂ are oromising candidates for use in single-component polymer solar cells with NIR photoresponse.展开更多
Hydrophilic dendrimers, especially poly（amidoamine）（PAMAM） dendrimers are widely applied in modifying fluorescent dyes to endow them with water solubility and biocompatibility for biologic fluorescence imaging.Com...Hydrophilic dendrimers, especially poly（amidoamine）（PAMAM） dendrimers are widely applied in modifying fluorescent dyes to endow them with water solubility and biocompatibility for biologic fluorescence imaging.Common preparation strategies of fluorescent dendrimers including encapsulating dyes or attaching dyes at periphery of dendrimers might cause uncertain constituent and lower biocompatibility. Here, we have developed a series of watersoluble fluorescent dendrimers with dye as core and fanshaped PAMAM as arms. Carboxylated perylene bisimides（PBI） dye and squarylium indocyanine（SICy） dye were conjugated with PAMAM dendrons by amidation to obtain a series of fluorescent dendrimers with enhanced water-solubility. Two PBI based dendrimers（PBI-G2.5 and PBI-G1.5）were chosen as model compounds for further optical, selfassembly and biological studies. In aqueous environment,PBI-G2.5 exhibited strong fluorescence, small size（~30 nm）and slightly positive surface charge（~2.46 mV）, which are ideal for biomedical applications. In vitro assays demonstrated that PBI-G2.5 nanoparticles accumulated in the cytoplasm of He La cells with rapid cellular uptake. The strong fluorescence in He La cells remained for over 48 h. To conclude, our study provides an effective strategy for preparing water-soluble fluorescent dendrimers towards long-term live cell imaging.展开更多
基金Project(50573019)support by the National Natural Science Foundation of China
文摘An intermediate compound 2, 4-bis（laurylamino）-6-（1-（2-aminoethyl）-piperazine）-1, 3, 5-triazine was prepared by stepwise nucleophilic substitution on triazine ring by lauryl amine and subsequently 1-（2-aminoethyl）-piperazine. Then imidization of perylene-3, 4, 9, 10-tetracarboxylic acid dianhydride with 2,4-bis（laurylamino）-6-（1-（2-aminoethyl）-piperazine）-1, 3, 5-triazine was carried out to afford a novel perylene derivative bearing two melamine blocks （S2） and 1, 6, 7, 12-tetra（4-tert-butyl phenoxy）-perylene-3, 4, 9, 10-tetracarboxylic acid bisimide （S1. The hydrogen-bonding interactions between S1 and S2 were investigated by IH NMR spectrum, UV/Vis spectrum and fluorescence spectrum. The influences on the morphologies of S1·S2 aggregates were investigated. The results show that well-defined nanofibers with a diameter of about 100 nm can be obtained by self-assembly between S1 and S2 only in CH2Cl2 solution. Based on these results, guidelines for the molecular design and self-assembly of supramolecular polymer materials are presented.
基金This work was supported by National Natural Science Foundation of China and Shanghai Science Committee.
文摘Novel perylene bisimide dyes bay-functionalized with naphthalimide chromophores have been prepared conveniently by coupling of 1,8-naphthalimide and dibromoperylene bisimides. Their optical properties were investigated by UV-vis and fluorescence spectroscopy. The absorption spectra of these compounds showed wide spectral responses from 300 to 700 nm, which would be potentials for application as organic solar cells.
基金This research was supported by the National Natural Scientific Foundation of China(No.90101008)973 project(No.2002CB613401)of the MST of P.R.China.
文摘A perylene bisimide dye covalently bonded with a hydrogen-bond formation group of 1, 3, 5-triazine-2, 4-diamine has been synthesized. Its casting films show a charge carrier mobility over 10^-3 cm^2/Vs, which is in the range of the highest values found for other promising charge transport materials suitable for solution processable technique.
基金National Natural Science Foundation of China(Nos.92163128,52073016,52163018)the Open Project of State Key Laboratory of Organic-Inorganic Composites,China(No.oic-202201006)the Fund of the Academy of Sciences of Jiangxi Province,China(Nos.2022YJC2017,2021YSBG22034,2021YSBG22033).
文摘By combining stable radical tetramethylpiperidine nitrogen oxide(TEMPO)as end groups and perylene bisimide(PBI)as the core,a small molecular cathode interlayer(CIL)(PBI-TEMPO)was synthesized.Detailed physical-chemical characterizations indicate that PBI-TEMPO can form smooth film,owns low unoccupied molecular orbital(LUMO)level of−3.67 eV and can reduce the work function of silver electrode.When using PBI-TEMPO as CIL in non-fullerene organic solar cells(OSCs),the PM6:BTP-4Cl based OSCs delivered high power conversion efficiencies(PCEs)up to 17.37%,higher than those using commercial PDINO CIL with PCEs of 16.95%.Further device characterizations indicate that PBI-TEMPO can facilitate more efficient exciton dissociation and reduce charge recombination,resulting in enhanced current density and fill factor.Moreover,PBI-TEMPO displays higher thermal stability than PDINO in solution.When PBI-TEMPO and PDINO solution were heated at 150℃ for 2 h and then were used as CIL in solar cells,PBI-TEMPO-based OSCs provided a PCE of 15%,while PDINO-based OSCs only showed a PCE of 10%.These results demonstrate that incorporating TEMPO into conjugated materials is a useful strategy to create new organic semiconductors for application in OSCs.
基金supported by the National Natural Science Foundation of China(NSFC)(51473009)the International Science&Technology Cooperation Program of China(2014DFA52820)
文摘Two perylene bisimides based non-fullerene small molecules, H-DIPBI and B-DIPBI, are applied into inverted planar heterojunction perovskite solar cells. The power conversion efficiency up to 11.6% has been achieved for device with B-DIPBI,indicating that non-fullerene acceptor can function as the electron transport layer to replace PCBM in perovskite solar cells.
基金supported by the Natural Science Foundation of China(21820102005,22132002)111 project(B14041)+1 种基金the Fundamental Research Funds for the Central Universities of China(2019TS033,GK202001005 and GK202003034)the Youth Innovation Team of Shaanxi Universities。
文摘Integrating multiple photosensitive properties into an“all-in-one”photosensitizer(PS)shows great promise for the treatment of cancers owing to synergistic effect among them.However,the development of such PSs,especially those that need a single laser source,remains a challenge.Herein,we report an orchestration of electron donors and acceptors in a propeller-like pentad,PBI-4Cz,where four carbazole(Cz)units are covalently linked to the ortho-positions of the perylene bisimide(PBI)core.Strong intramolecular donor-acceptor interaction significantly quenches the luminescence and largely extends the absorption spectra to near-infrared region.Excited-state dynamics investigated via femto-and nano-second transient absorption spectroscopy revealed exclusive charge separation of the PBI-4Cz within initial 0.5 ps when photoexcited regardless of which intermediate is involved.Energy dissipation of the resulting charge-separated state(PBI^(•−)-4Cz^(•−))is subjected to the toggle between intersystem-crossing toward excited triplet states and charge recombination toward ground states.Relative importance of the two pathways can be tuned by micro-environmental polarity,which endows PBI-4Cz remarkable performances of singlet-oxygen generation(>90.0%)in toluene and photothermal conversion(∼28.6%)in DMSO.Harnessing intrinsic photostability and excited-state processes of heavy-atom-free PBI derivatives not only holds a promise for multifunctional phototheranostics,but also provides a prototype for designing high-performance PSs with tunable photoconversion pathways.
基金financially supported by the Recruitment Program of Global Youth Experts of Chinathe National Natural Science Foundation of China(Nos.51603209 and 21574138)the Strategic Priority Research Program(No.XDB12030200)of the Chinese Academy of Sciences
文摘Perylene bisimide （PBI） unit has been widely used to design conjugated materials, which can be used as electron acceptor in organic solar ceils due to its strong electron-deficient ability. In this work, a conjugated polymer based on PBI dimer as monomer was designed, synthesized, and compared to the conjugated polymer containing single PBI as repeating units. The two conjugated polymers were found to have similar molecular weight, absorption spectra and energy levels. Density functional theory calculation revealed that the PBI dimer-based polymer exhibited highly twisted conjugated backbone due to the large dihedral angle between the two PBI units. The PBI-based polymers as electron acceptor were applied into polymer-polymer solar cells, in which PBI dimer-based polymer solar cells were found to show a high short circuit current density （Jsc = 11.2 mA.cm-2） and a high power conversion efficiency （PCE） of 4.5%. In comparison, the solar cells based on PBI-based polymer acceptor only provided a dsc of 7.2 mA.cm-2 and PCE of 2.5%. The significantly enhanced PCE in PBI dimer-based solar cells was attributed to the mixed phase in blended thin films, as revealed by atom force microscopy. This study demonstrates that PB! dimer can be used to design polymer acceptors for high performance polymer- polymer solar cells.
文摘Designed and synthesized a new highly water soluble N,N^1-bis（2-（（5-（（dimethylamino）methyl）furan-2-yl）methylthio）ethyl）-perylene -3,4,9,10-tetracarboxylic diimide from 2-（（5-（（dimethylamino）methyl）furan-2-yl）methylthio）ethanamine and perylene-3,4,9,10- tetracarboxylic dianhydride.The compound was characterized by ~1H,^（13）C,2D NMR,mass and IR techniques.The compound is highly fluorescent with good solubility in water and other polar solvents.
基金supported by the National Natural Science Foundation of China (51573055, 51373054, 21334002, 51403063)National Basic Research Program of China (2014CB643504)+2 种基金Fundamental Research Funds for the Central UniversitiesChina Postdoctoral Science Fund (2014M562174)Introduced Innovative Research & Development Team of Guangdong (201101C0105067115)
文摘Neutral perylene bisimides(PBI) are well-known n-type organic semiconductors, with number of challenging electronic properties in their neutral and reduced states. We report the characteristic electronic properties of PBI anionic films. We unexpectedly discovered that pristine PBI dianion film showed p-type character, while oxidized dianion film(dominant neutral state with few radical anions) showed normal n-type semiconductor character based on Seebeck effect measurements. Both kinds of films exhibit high electrical conductivity with a potential for thermoelectric applications. The mechanism of polarity reversal is proposed.
基金supported by the Recruitment Program of Global Youth Experts of Chinasupported by the National Natural Science Foundation of China(Nos. 21574138, 51603209 and 91633301)the Strategic Priority Research Program(No. XDB12030200) of the Chinese Academy of Sciences
文摘In this work, star-shaped perylene bisimide（PBI） derivatives with spiro-aromatic cores linked with ethynyl units were developed as electron acceptors for non-fullerene organic solar cells. The ethynyl linkers were found to enhance the planarity of the conjugated backbone, resulting in high electron mobilities and near-infrared absorption. The ethynyl-linked PBI acceptors showed high power conversion efficiencies（PCEs） up to 4.27% due to the high short-circuit current density（Jsc） of 8.52 mA/cm^2 and fill factor（FF） of 0.59, while the PBI acceptor without ethynyl units provided a low PCE of 3.57% in nonfullerene solar cells. The results demonstrate that ethynyl units can be applied into designing new PBI electron acceptors with improved charge transport properties and photovoltaic performance.
基金We ack no wledge the fundi ng from the Nati onal Natural Science Foundation of China(21820102005),111 project(B14041)the Fun dame ntal Research Funds for the Cen tral Un iversities(GK202001005 and GK202003034)+1 种基金the Innovation Capability Support Program of Shaanxi(2021TD-18)the Youth Innova-tion Team of Shaanxi Universities.
文摘Rapid and real-time mon itoring of food quality plays critical roles in the food industry and for the gen era I public health.Herei n,we specially synthesized a new perylene bisimide(PBI)derivative(PCB-EpE)composed of two PBI units and a rigid o-carborane linker,which was further employed in constructi ng a con ceptual fluoresce nt film sen sor for evaluati ng fish fresh ness.Photophysical studies indicate that PCB-EpE displays an open"Z-type"molecular configuration in chloroform and a closed"△-type"configuration in methyl cyclohexa ne.Comparatively,"Z-type"molecular configurati on possesses higher fluoresce nee qua ntum yield and is more sen sitive toward volatile basic nitrogen(VBN).
基金supported by the National Natural Science Foundation of China(grant nos.51521002 and 21905098)the China Postdoctoral Science Foundation(grant no.2018M643067)the 21Hong Kong-Macao Joint Laboratory of Optoelectronic and Magnetic Functional Materials(grant no.2019B121205002).
文摘Cathodic electrochromic materials realized by n-type doping of conducting polymers are scarce.Even with limited cases reported in the literature,long-term stability is an urgent problem to be solved.Herein,we report a high performance and stable cathodic electrochromic material,poly(Th-Cl-PBI),based on a perylene bisimide function core.Due to its high electropolymerization efficiency and low steric hindrance of thiophene groups,perylene bisimide,which generally does not dissolve and form film easily,can grow to the sufficient thickness of 350 nm for wide-range spectral modulation and large-capacity energy storage.The optical contrast of optimized film with a thickness of 240 nm reaches as high as 69.1% at 520 nm,94.1% at 760 nm,and 95.7% at 680 nm.Theoretical simulation based on the Lambert–Beer law also verifies this optical contrast dependent on film thickness.Besides,during the transition between the neutral state and radical anion state,it maintains 90.2% of the electrochemical activity after 4000 cycles,and the transmittance spectrum remains stable after 2000 cycles.The cation size effect on cathodic electrochromic process and cyclic stability has been investigated.
基金the Natural Science Foundation of China(nos.21820102005,21527802,and 21673133)China 111 project(no.B14041)Program for Changjiang Scholars and Innovative Research Team in University(no.IRT-14R33).
文摘We have fabricated a new perylene bisimide(PBI)folda-dimer(BPBI-CB-1)by tethering two PBI moieties to the ortho-carbon positions of a carborane unit.The synthesized compound adopted distinct configurations in different solvents with dual emissions as its characteristic.The two PBI moieties in the molecule appeared either in a weakly interacted,monomer-like state or brought into close π-π contact with each other,forming an interacted stacking state.The equilibrium between these two states was governed by the nature of solvents and testing temperature.Spectroscopic and theoretical studies concluded that dual emission bands originated from intramolecular monomer-like and stacking states,respectively.Remarkably,in a solvent like 1,2-dichloroethane(DCE),both emission intensities increased with rising temperatures.The positive temperature response of the monomer emission was ascribed to an increased amount of monomer-like population,owing to its endothermic energy state,while the excimer emission was rationalized by increased population of the bright exciton state,resulting in an increased emission yield that compensated the diminished population of the stacking state.To our knowledge,this is the first report on positive temperature-responsive dual emissions associated with the synergism of intramolecular intersubunit aggregation/dissociation and excimer transformation.
文摘Supramolecular polymerization properties have been studied for a series of perylene bisimide(PBI)dyes containing identical hydrogen-bonding amide groups in imide positions but variable number or size of alkoxy substituents in bay-positions.
基金supported by the Science and Technology Development Foundation of China Academy of Engineering Physics (Nos.2012A0302015,2012B0302050 and 2013B0302051)Doctoral Fund of Southwest University of Science and Technology (No.13zx7133)
文摘Fourfold benzocyclobutene-functionalized perylene bisimide（PBI 4） has been synthesized and its structure was characterized by FTIR,MS and NMR.PBI 4 can react either with itself,or the appropriate dienophiles to form the corresponding products under appropriate temperature.The polymer film obtained from the reaction of PBI 4 with methyl vinyl silicone rubber possessed excellent film forming properties including flatness.The optical properties of PBI 4 and polymer film obtained from the reaction of PBI 4 and methyl vinyl silicone rubber have been determined by UV/vis and fluorescence spectroscopy.
基金financially supported by the National Natural Science Foundation of China(No.21774107)the Jiangsu Government Scholarship for Overseas Studiesthe Initial Scientific Research Foundation of Yancheng Institute of Technology(No.KJC2014002)
文摘A novel perylene tetracarboxylic acid bisimide（PTCBI） in-chain polyethylene（PE） was first prepared via acyclic diene metathesis（ADMET） polymerization of PTCBI-functionalized α,ω-diene monomer. The polymers could spontaneously self-assemble into hollow cylindrical structures in which the π-π interaction between adjacent PTCBI moieties was enhanced and the electron mobility was possibly promoted. The hydrogenation of as-obtained polymer was readily accomplished, affording the desired precision PTCBI in-chain PE with a saturated backbone, which showed high glass transition temperature（Tg = 63 °C）, relatively wide range of light absorption（λ = 200-575 nm）, and higher LUMO level（-3.62 e V）. It can therefore serve as a superior model for facile construction of functional polyolefin and soluble PTCBI polymer with ordered architecture.
基金Supported by the National Natural Science Foundation of China(Nos.51503037,51822308,51733004,21661132006)the Program for New Century Excellent Talents in Fujian Province Universities,China,the Fund of the Youth Innovation Promotion Association of the Chinese Academy of Sciences and the Education and Scientific Research Project for Young and Middle-aged Teachers in Fujian Province,China(No.JT180633).
文摘Copper/oxalic diamide-promoted dimerization of tetrachlorinated perylene bisimide to construct highly-fused diperylene bisimides through Ullmann coupling and zipper-mode double C—H activation has been developed in this study.This one-step reaction combining homocoupling with C—H activation proceeded smoothly under the action of inexpensive metal-ligand system.This protocol is expected to expand the available synthetic tools for condensed ring systems of perylene bisimide(PBIs).
文摘An isoindigo-based ＂double-cable＂ conjugated polymer bearing perylene bisimide side units was developed via Stille polymerization for application in single-component polymer solar cells, in which a power conversion efficiency of 1% with broad photo-response from 300 nm to 800 nm was achieved. There is no evidence of large phase separation confirmed by AFM images and photoluminescence （PL） spectra. The space charge limit current measurements and light intensity dependence measurements indicate that the low electron mobility and the significant recombination of pho- togenerated charge carriers in active layer mainly account for the low performance of our solar cells. Our results suggest that these ＂double-cable＂ are oromising candidates for use in single-component polymer solar cells with NIR photoresponse.
基金financially supported by the National Natural Science Foundation of China (21774007, 21574009 and 51521062)the Higher Education and High-quality and World-class Universities (PY201605)
文摘Hydrophilic dendrimers, especially poly（amidoamine）（PAMAM） dendrimers are widely applied in modifying fluorescent dyes to endow them with water solubility and biocompatibility for biologic fluorescence imaging.Common preparation strategies of fluorescent dendrimers including encapsulating dyes or attaching dyes at periphery of dendrimers might cause uncertain constituent and lower biocompatibility. Here, we have developed a series of watersoluble fluorescent dendrimers with dye as core and fanshaped PAMAM as arms. Carboxylated perylene bisimides（PBI） dye and squarylium indocyanine（SICy） dye were conjugated with PAMAM dendrons by amidation to obtain a series of fluorescent dendrimers with enhanced water-solubility. Two PBI based dendrimers（PBI-G2.5 and PBI-G1.5）were chosen as model compounds for further optical, selfassembly and biological studies. In aqueous environment,PBI-G2.5 exhibited strong fluorescence, small size（~30 nm）and slightly positive surface charge（~2.46 mV）, which are ideal for biomedical applications. In vitro assays demonstrated that PBI-G2.5 nanoparticles accumulated in the cytoplasm of He La cells with rapid cellular uptake. The strong fluorescence in He La cells remained for over 48 h. To conclude, our study provides an effective strategy for preparing water-soluble fluorescent dendrimers towards long-term live cell imaging.
