供/吸电子基团共轭桥联的双BODIPY衍生物的合成及性能  

Synthesis and Properties of Symmetrical Donor or Acceptor Unit Conjugate Linked BODIPY Derivatives

作　　者：彭再喜 廖俊旭[2] 徐勇军[2] 赵鸿斌[2] 彭敏[2] 崔云增 宁静恒[1] 

机构地区：[1]长沙理工大学化学与生物工程学院,长沙410004 [2]东莞理工学院化学与环境工程学院,东莞523808

出　　处：《高等学校化学学报》2015年第6期1094-1099,共6页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:21342003);广东省自然科学基金(批准号:2014A030313630);广东省教育厅广东省高等学校高层次人才项目[批准号:粤财教(2013)246号]资助~~

摘　　要：设计合成了4种对称的以不同供/吸电子基团为共轭桥、两端连接meso位苯或噻吩取代的新型氟化硼二吡咯甲川(BODIPY)衍生物;通过1H NMR,13C NMR和MS等手段对其进行了结构表征;并采用紫外吸收光谱、荧光发射光谱及循环伏安(CV)等方法研究了其光电性能.紫外光谱数据表明,BODIPY结构具有明显的特征吸收,中间的桥联基团无论是强供电子的苯并二噻吩(BDT)还是强吸电子的苯并噻二唑(BT)均不能使整个分子产生明显的分子内电子迁移(ICT).另一方面,meso位的取代基可与BODIPY核产生微弱的ICT,且meso位噻吩取代的分子比meso位苯环取代的分子表现出更强的ICT.紫外光谱数据和电化学测试结果表明,meso位噻吩取代的分子比meso位苯环取代的分子具有更低的氧化电位和更窄的能隙.Four novel symmetrical 4,4＇-difluoro4-bora-3a, 4a-diaza-sindacene （BODIPY） derivatives were synthesized. These BODIPY derivatives bear different donor or acceptor units as conjugate bridge, and the BODIPYs meso-position substituted by thiophene or benzene as the termini groups. The structures of all the compounds were identified by l H NMR, 13C NMR and MS techniques. The photopbysical properties of these compounds were measured by the UV-Vis absorption and the fluorescence emission spectrophotometer. And the electrochemical properties were investigated by the cyclic voltammetry. The results of absorption spectra confirmed that these BODIPYs had a characteristic absorption peak, and the conjugate bridges had little influence on the intramolecular charge-transfer（ICT） interaction neither used as donor nor acceptor. On the other hand, meso-position substituentes have a weak influence on the ICT interaction in the BODIPYs, and meso-position thiophene substituted ones have raised more intensive ICT than the meso-position benzene substituted ones. Both the absorption spectra and cyclic voltammetry data indicate that BODIPYs with raeso- thiophene substitutuents possess a lower oxidation potential and a narrower band gap than those meso-position benzene ones.

关 键 词：氟化硼二吡咯甲川衍生物 共轭桥 供/吸电子基团 光电性能 

分 类 号：O621[理学—有机化学]