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2021 , Vol. 41 >Issue 6: 2401 - 2407

DOI: https://doi.org/10.6023/cjoc202012011

研究论文

含单一芘基冠状共轭分子的合成、表征和光物理性质

  • 李璟奭 ,
  • 庄桂林 ,
  • 黄强 ,
  • 王进义 ,
  • 吴亚宇 ,
  • 杜平武
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  • a 中国科学技术大学化学与材料科学学院 合肥 230026
    b 浙江工业大学化学工程学院 杭州 310032

收稿日期: 2020-12-05

  修回日期: 2021-02-08

  网络出版日期: 2021-02-26

基金资助

国家重点研发计划(2017YFA0402800); 国家自然科学基金(21971229); 国家自然科学基金(51925206); 国家自然科学基金(U1932214); 浙江省自然科学基金(LR19B010001)

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A Conjugated Molecular Crown Containing a Single Pyrenyl Unit: Synthesis, Characterization, and Photophysical Properties

  • Jingshi Li ,
  • Guilin Zhuang ,
  • Qiang Huang ,
  • Jinyi Wang ,
  • Yayu Wu ,
  • Pingwu Du
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  • a Department of Materials Science and Engineering, University of Science and Technology of China, Hefei 230026
    b College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032
*Corresponding author.E-mail:

Received date: 2020-12-05

  Revised date: 2021-02-08

  Online published: 2021-02-26

Supported by

National Key Research and Development Program of China(2017YFA0402800); National Natural Science Foundation of China(21971229); National Natural Science Foundation of China(51925206); National Natural Science Foundation of China(U1932214); Zhejiang Provincial Natural Science Foundation(LR19B010001)

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摘要

由于独特的结构和物理性质, 大环共轭化合物引起了研究者广泛关注. 报道了含单个芘单元的[7]环对苯基-2,7-芘([7]CPPPy2,7)大环分子的合成方法和光物理性质. 通过含弯曲结构的前驱体和芘的双硼酸酯化底物的Suzuki-Miyanra偶联反应, 加入亚锡酸还原芳构化, 该分子的成功制备被质谱及系列相关核磁共振谱图等表征证实. 新化合物的光物理性质通过紫外-可见光谱等测试方法进一步研究, 其最大紫外吸收峰出现在326 nm, 与理论计算结果相吻合. 在350 nm波长光激发下, 其荧光激发峰值出现在492 nm处. 计算结果表明, 该化合物的应变能为299.17 kJ•mol–1.

关键词： 共轭大环分子; 分子环; 多环芳烃; 芘

本文引用格式

李璟奭 , 庄桂林 , 黄强 , 王进义 , 吴亚宇 , 杜平武 . 含单一芘基冠状共轭分子的合成、表征和光物理性质[J]. 有机化学, 2021 , 41(6) : 2401 -2407 . DOI: 10.6023/cjoc202012011

Abstract

Macrocyclic π-conjugated materials have attracted much attention due to their unique structures and physical properties. The synthetic methods and physical properties of a π-extended molecular crown containing a single pyrenyl unit, cyclo[7]paraphenylene-2,7-pyrenylene ([7]CPPPy 2,7), were report. This macrocycle was achieved by a rationally designed Suzuki-Miyanra coupling of a curved precursor and pyrene-2,7-bis(boronate), followed by reductive aromatization with stannous acid, and confirmed by various physical characterizations, such as HR-MS and a series of NMR spectroscopies. The photophysical properties of [7]CPPPy2,7 were further studied by UV-vis spectroscopy and other analysis, and its maximum absorption peak was located at 326 nm, which was consistant with density functional theory (DFT) calculations. The fluorescence emission spectrum of [7]CPPPy2,7 was further studied. Under 350 nm excitation, the emission peak appeared at 492 nm. The computational result indicates the strain energy of [7]CPPPy2,7 is as high as 299.17 kJ•mol–1.

Key words： π-conjugated macrocycle; molecular crown; polyaromatic hydrocarbon; pyrene

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