Thienoacenes is one of most important groups of semiconducting materials due to the high stability and superior mobility.However,there are scarce studies on the emission properties of thienoacenes to date.Herein,we sy...Thienoacenes is one of most important groups of semiconducting materials due to the high stability and superior mobility.However,there are scarce studies on the emission properties of thienoacenes to date.Herein,we synthesized fluorinated and chlorinated dibenzo[d,d’]thieno[3,2-b;4,5-b’]dithiophenes(DBTDTs)derivatives F6-DBTDT and Cl6-DBTDT by sulfoxide cyclization,significantly lowering the energy levels relative to the parent compound DBTDT.According to single crystal structure analysis,F6-DBTDT molecules adopt one-dimensional slipped stacking with closeπ-πinteractions of 3.43Å(1Å=0.1 nm),which is different from the parent compound DBTDT with herringbone stacking motif.Interestingly,the halogenated DBTDT derivatives exhibit enhanced emission properties both in solution and in the solid state,opening up possiblities to improve photoluminescence of thienoacences by halogenation.展开更多
A novel semiconductor, dihexyl-substituted pentathienoacene(C6-PTA) is designed and synthesized in five steps with the total yield up to 25.2%. The introduction of hexyl chains endow the thin film semiconductor with a...A novel semiconductor, dihexyl-substituted pentathienoacene(C6-PTA) is designed and synthesized in five steps with the total yield up to 25.2%. The introduction of hexyl chains endow the thin film semiconductor with about threefold increase in carrier mobility and one to three orders of magnitude improvement in current on/off ratio. Furthermore, single crystal FETs based on C6-PTA exhibited mobility up to 0.64 cm^2 V^(-1) s^(-1), which is over 50 times higher than the thin film counterpart. The results indicate clearly that C6-PTA is a promising organic semiconductor with high stability.展开更多
Three acceptor-donor-acceptor （A-D-A） conjugated oligomers, i.e., O1, 02 and 03, have been synthesized using diketopyrrolopyrrole （DPP） as an electron-acceptor unit, and naphtho[1,2-b：5,6-b＇]dithiophene （NDT）,...Three acceptor-donor-acceptor （A-D-A） conjugated oligomers, i.e., O1, 02 and 03, have been synthesized using diketopyrrolopyrrole （DPP） as an electron-acceptor unit, and naphtho[1,2-b：5,6-b＇]dithiophene （NDT）, anthra[1,2-b：5,6- b＇]dithiophene （ADT） or dithieno[3,2-b：Y,2＇-b＇]naphtbo[1,2-b：5,6-b＇]dithiophene （DTNDT） as electron-donor unit. These oligomers exhibit identical highest occupied molecular orbital （HOMO） and lowest unoccupied molecular orbital （LUMO） energy levels, which were ca. -5.1 and -3.3 eV, respectively. Upon thermal annealing, all three oligomers formed thin films with ordered microstructures, and their organic thin film transistors （OTFTs） exhibited p-type transport behavior. The mobility was increased with an extension of the size of D-units. 03 showed the best OTFT performance with the mobility of up to 0.20 cm2·V-1 ·s-1. The film quality of 03 was improved by adding 1 wt% poly（methylmethacrylate） （PMMA）. In consequence, the mobility of the O3-based devices was further enhanced to 0.30 cm2·V-1 ·s-1.展开更多
Organic single crystals(OSCs)offer a unique combination of both individual and collective properties of the employed molecules,but it remains highly challenging to achieve OSCs with both high mobilities and strong flu...Organic single crystals(OSCs)offer a unique combination of both individual and collective properties of the employed molecules,but it remains highly challenging to achieve OSCs with both high mobilities and strong fluorescence emissions for their potential applications in multifunctional optoelectronics.Herein,we demonstrate the design and synthesis of two novel triphenylamine-functionalized thienoacenes-based organic semiconductors,4,8-distriphenylamineethynylbenzo[1,2-b:4,5-b′]dithiophene(4,8-DTEBDT)and 2,6-distriphenylamineethynylbenzo[1,2-b:4,5-b′]dithiophene(2,6-DTEBDT),with high-mobility and strong fluorescence emission.The two compounds show the maximum mobilities up to 0.25 and 0.06 cm^(2) V^(-1) s^(-1),the photoluminescence quantum yields(PLQYs)of 51% and 45%,and the small binding energies down to 55.13 and 58.79 meV.The excellent electrical and optical properties ensured the application of 4,8-DTEBDT and 2,6-DTEBDT single crystals in ultrasensitive UV phototransistors,achieving high photoresponsivity of 9.60×105 and 6.43×10^(4) AW^(-1),and detectivity exceeding 5.68×10^(17) and 2.99×10^(16) Jones.展开更多
基金supported by the Fundamental Research Funds for the Central Universities,China(No.buctrc202103)the National Natural Science Foundation of China(Nos.21975263,22171019,52373170)+2 种基金the Project of the China Petroleum and Chemical Corporation(No.222131)the Open Project Programs of Wuhan National Laboratory for Optoelectronics,China(No.2021WNLOKF005)the Project of the State Key Laboratory of Fine Chemicals(Dalian University of Technology),China(No.KF2201).
文摘Thienoacenes is one of most important groups of semiconducting materials due to the high stability and superior mobility.However,there are scarce studies on the emission properties of thienoacenes to date.Herein,we synthesized fluorinated and chlorinated dibenzo[d,d’]thieno[3,2-b;4,5-b’]dithiophenes(DBTDTs)derivatives F6-DBTDT and Cl6-DBTDT by sulfoxide cyclization,significantly lowering the energy levels relative to the parent compound DBTDT.According to single crystal structure analysis,F6-DBTDT molecules adopt one-dimensional slipped stacking with closeπ-πinteractions of 3.43Å(1Å=0.1 nm),which is different from the parent compound DBTDT with herringbone stacking motif.Interestingly,the halogenated DBTDT derivatives exhibit enhanced emission properties both in solution and in the solid state,opening up possiblities to improve photoluminescence of thienoacences by halogenation.
基金financial support from the Ministry of Science and Technology of China (Nos. 2015CB856502, 2016YFB0401100 and 2017YFA0204503)the National Natural Science Foundation of China (Nos. 51733004, 51822308, 51725304, 51633006, 21661132006)+2 种基金the Strategic Priority Research Program (No. XDB12000000)the Youth Innovation Promotion Association of the Chinese Academy of Sciences, Startup Foundation for Doctors of China West Normal University (No. 15E007)Open Foundation of Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province (No. CSPC2015-1-1)
文摘A novel semiconductor, dihexyl-substituted pentathienoacene(C6-PTA) is designed and synthesized in five steps with the total yield up to 25.2%. The introduction of hexyl chains endow the thin film semiconductor with about threefold increase in carrier mobility and one to three orders of magnitude improvement in current on/off ratio. Furthermore, single crystal FETs based on C6-PTA exhibited mobility up to 0.64 cm^2 V^(-1) s^(-1), which is over 50 times higher than the thin film counterpart. The results indicate clearly that C6-PTA is a promising organic semiconductor with high stability.
基金financially supported by National Basic Research Program of China(973 Program,No.2014CB643504)of Chinese Ministry of Science and Technologythe National Natural Science Foundation of China(No.51333006)the Strategic Priority Research Program of the Chinese Academy of Sciences(No.XDB12010300)
文摘Three acceptor-donor-acceptor （A-D-A） conjugated oligomers, i.e., O1, 02 and 03, have been synthesized using diketopyrrolopyrrole （DPP） as an electron-acceptor unit, and naphtho[1,2-b：5,6-b＇]dithiophene （NDT）, anthra[1,2-b：5,6- b＇]dithiophene （ADT） or dithieno[3,2-b：Y,2＇-b＇]naphtbo[1,2-b：5,6-b＇]dithiophene （DTNDT） as electron-donor unit. These oligomers exhibit identical highest occupied molecular orbital （HOMO） and lowest unoccupied molecular orbital （LUMO） energy levels, which were ca. -5.1 and -3.3 eV, respectively. Upon thermal annealing, all three oligomers formed thin films with ordered microstructures, and their organic thin film transistors （OTFTs） exhibited p-type transport behavior. The mobility was increased with an extension of the size of D-units. 03 showed the best OTFT performance with the mobility of up to 0.20 cm2·V-1 ·s-1. The film quality of 03 was improved by adding 1 wt% poly（methylmethacrylate） （PMMA）. In consequence, the mobility of the O3-based devices was further enhanced to 0.30 cm2·V-1 ·s-1.
文摘Organic single crystals(OSCs)offer a unique combination of both individual and collective properties of the employed molecules,but it remains highly challenging to achieve OSCs with both high mobilities and strong fluorescence emissions for their potential applications in multifunctional optoelectronics.Herein,we demonstrate the design and synthesis of two novel triphenylamine-functionalized thienoacenes-based organic semiconductors,4,8-distriphenylamineethynylbenzo[1,2-b:4,5-b′]dithiophene(4,8-DTEBDT)and 2,6-distriphenylamineethynylbenzo[1,2-b:4,5-b′]dithiophene(2,6-DTEBDT),with high-mobility and strong fluorescence emission.The two compounds show the maximum mobilities up to 0.25 and 0.06 cm^(2) V^(-1) s^(-1),the photoluminescence quantum yields(PLQYs)of 51% and 45%,and the small binding energies down to 55.13 and 58.79 meV.The excellent electrical and optical properties ensured the application of 4,8-DTEBDT and 2,6-DTEBDT single crystals in ultrasensitive UV phototransistors,achieving high photoresponsivity of 9.60×105 and 6.43×10^(4) AW^(-1),and detectivity exceeding 5.68×10^(17) and 2.99×10^(16) Jones.
