喹唑啉酮类化合物的合成及光电性能

Syntheses and Optical Properties of Quinazolinone Derivatives

摘要:

本文以5-溴靛红和2,5-二溴吡啶为原料，合成2,8-二溴11H吡啶并[2,1-b]喹唑-11-酮，再通过suzuki偶联反应在分子两侧进行修饰，合成3个喹唑啉酮衍生物，收率在68% ~ 85%，其结构经1H NMR、13C NMR和MS确证。通过紫外可见吸收光谱，荧光发射光谱考查了其光学性能，用循环伏安法和理论计算考查了其的电化学性质。结果表明，在喹唑啉酮母体分子两侧接入供电子基团延长了分子的π共轭体系，增加了喹唑啉酮母体两侧的空间位阻，减少分子间的π-π堆积，两侧的供电子基团与喹唑啉酮母体形成了推挽结构，有利于分子内的电子转移，减少电子由基态到激发态的跃迁能。该类化合物是一类潜在的三阶非线性光学功能材料。

Abstract:

2,8-dibromo-11H-pyrido[2,1-b]quinazolin-11-one was synthesized from 5-bromoisatin, 2,5-dibromopyridine. Then three new quinazolinone derivatives with yields between 68% and 85% were synthesized via suzuki coupling, structures of the compounds were identified by nuclear magnetic resonance spectroscopy and mass spectroscopy．Their optical physical properties were investigated by UV-Vis and fluorescence spectroscopy．Their electrochemical properties were studied by cyclic voltammetry and theoretical calculation methods. The results showed that the introduction of donor groups on the planar structure of parent ring extend the π-conjugation system, reduced the π-π intermolecular stacking of parent ring compound, and the formation of push-pull structure by connecting donor groups to quinazolinone backbone decreased energy gap of entire molecule. These quinazolinone derivatives are a kind of potential third-order nonlinear optical materials．