摘要
建立了一个基于芳叉丙二腈的高活性迈克尔系统2,2′-[(5-叔丁基-2-羟基-1,3-苯撑)二甲川]双丙二腈(1),能迅速吸收空气中的水,生成稳定的氧杂迈克尔加成产物2-[5-叔丁基-3-(2,2-二腈基-1-羟乙基)-2-羟基苄叉]丙二腈(2).在二甲亚砜(DMSO)中,各种碱性催化剂都能使化合物2脱水生成化合物1,同时发射红色强荧光.在PBS缓冲溶液(pH=10)中,化合物2立即脱水生成化合物1,随后又缓慢加水转变为化合物2.加热吸附在硅胶上的化合物2的荧光由蓝色变为红色,温度降低后荧光又恢复为蓝色.因此,吸附了化合物2的硅胶可能发展成为一种热敏荧光材料.此外,吸附了化合物1的硅胶还对某些有机蒸汽具有荧光响应.
The phenols and alcohols as nucleophiles are common in oxa-Michael reaction,while H;O normally cannot react with Michael system 2,2′-{[5-(tert-butyl)-2-hydroxy-1,3-phenylene]bis(methaneylylidene)}dimalononitrile(1)was reported,which could rapidly absorb water in the air to afford a stable 2-[5-(tert-butyl)-3-(2,2-dicyano-1-hydroxyethyl)-2-hydroxybenzyli-dene]malononitrile(2)via oxa-Michael addition.The high activity of compound 1 resulted from the synergistic effect among the two dicyanovinyl groups and the one hydroxyl group.In dimethyl sulfoxide(DMSO),compound 2 could quickly dehydrate to give compound 1 in the presence of various alkaline catalysts.In PBS buffer(pH=10),compound 2 immediately converted to compound 1,and then converted back to compound 2 slowly.When heat the silica gel plate loading compound 2,the fluorescence conversion from blue to red were observed.Hence,compound 2 adsorbed on silica gel might be developed into a thermosensitive fluorescent material.In addition,compound 2 adsorbed on silica gel showed fluorescence responses to some organic vapors.
作者
李巧
赵洋
王恩举
LI Qiao;ZHAO Yang;WANG Enju(Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education,Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province,College of Chemistry and Chemical Engineering,Hainan Normal University,Haikou 571158,China)
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
2022年第3期90-96,共7页
Chemical Journal of Chinese Universities
基金
海南省自然科学基金(批准号:219MS043)资助。
关键词
氧杂迈克尔反应
芳叉丙二腈
吸湿反应
荧光性质
Oxa-Michael reaction
Arylidenemalononitrile
Moisture absorption reaction
Fluorescence property
