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第 35 卷第 12 期 精 细 化 工 Vol.35, No.12
2018 年 12 月 FINE CHEMICALS Dec. 2018

功能材料
喹唑啉酮类化合物的合成及光电性能

贾建洪，王文标，胡成坤，李 唐，叶孙斌，高建荣

（浙江工业大学 化学工程学院，浙江 杭州 310014）

摘要：以 5-溴靛红和 2,5-二溴吡啶为原料，合成了 2,8-二溴-11H-吡啶并[2,1-b]喹唑-11-酮（Ⅱ），再通过 Suzuki
偶联反应在分子两侧用三芳胺等供电子基团进行了修饰，合成了 3 个喹唑啉酮衍生物，收率在 68%~85%，其结
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构经 HNMR、 CNMR 和 MS 确证。通过 UV-Vis、FL 测试考察了其光学性能，用循环伏安法和理论计算考察
了其电化学性质。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，减少了分子间的 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，其中接入三芳胺基团的 2,8-双（4-（二苯基氨基）
苯基）-11H-吡啶并[2,1-b]喹唑-11-酮（Ⅲ a）的能带隙（E gap ）最小，为 2.2533 eV，而未修饰的喹唑啉酮母环（Ⅰ）
的能带隙 E gap 为 2.7231 eV。喹唑啉酮化合物的能带隙具有明显优势，该类化合物是一类潜在的三阶非线性光学
功能材料。
关键词：喹唑啉酮类；光学材料；推挽结构；功能材料
中图分类号：O626 文献标识码：A 文章编号：1003-5214 (2018) 12-2011-06

Synthesis and Optical Properties of Quinazolinone Derivatives

JIA Jian-hong, WANG Wen-biao, HU Cheng-kun, LI Tang, YE Sun-bin, GAO Jian-rong
（College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, Zhejiang, China）

Abstract: 2,8-Dibromo-11H-pyrido[2,1-b]quinazolin-11-one (Ⅱ) was synthesized from 5-bromoisatin with
2,5-dibromopyridine. Then three new quinazolinone derivatives with yields between 68% and 85% were
obtained via suzuki coupling reaction. These compounds were characterized by NMR and MS. 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 extended the π-conjugation system,
reduced the π-π intermolecular stacking of parent ring compound. Furthermore, the formation of push-pull
structure by connecting donor groups to quinazolinone backbone not only facilitated the intramolecular
electron transfer but also decreased the transition energy of electrons from the ground state to the excited
state. Among these compounds, the band gap (E gap ) of 2,8-bis(4-(diphenylamino)phenyl)-11H-pyrido[2,1-b]
quinazol-11-one (Ⅲa) with a triarylamine group incorporated was the smallest (2.2533 eV), while that of the
unmodified quinazolinone parent ring (I) was 2.7231 eV. These quinazolinone derivatives had obvious E gap
advantages, which were a kind of potential third-order nonlinear optical materials.
Key words: quinazolinone derivatives; optical materials; push-pull structure; functional materials
Foundation item: National Natural Science Foundation of China (21452001)

喹唑啉酮是一类较为常见的稠杂环化合物，在 炎、抗过敏、抗惊厥、镇静催眠、降血压和抗癌 [4-6] 。
很多天然和合成药物中都有类似的结构 [1-3] ，不同的 同时，喹唑啉酮作为一类分子内共轭的电子转移化
喹唑啉酮衍生物显示出多样的药理活性，如：抗发 合物，具有刚性的共面结构和良好的受电子能力，

收稿日期：2017-12-13; 定用日期：2018-04-02; DOI: 10.13550/j.jxhg.20171011
基金项目：国家自然科学基金（21452001）
作者简介：贾建洪（1972—），男，副教授，硕士生导师，E-mail：zgdjjh@163.com。