HJCET  >> Vol. 3 No. 3 (May 2013)

    Synthesis of Novel Organic Conjugated Small Molecules Containing Heteroatoms (N, S)

  • 全文下载: PDF(352KB) HTML    PP.100-104   DOI: 10.12677/HJCET.2013.33019  
  • 下载量: 2,149  浏览量: 6,531  


何春阳,薛敏钊,张 帆:上海交通大学化学化工学院,上海

硫氮杂原子烷基链有机共轭小分子Heteroatoms (N S); Alkyl Chains; Organic Conjugated Small Molecules


设计并合成了一类富含硫氮杂原子的有机共轭小分子。在低温下,利用噻吩锂化以及与对应的卤代烷烃反应,引入不同的烷基链,进一步溴代后,制备相应格式试剂并与另一反应物1,2,4,5-四((S)-2’-吡啶酮)苯反应,得到重要中间体,最后通过水合肼还原关环,得到目标化合物。利用上述高效、简单的制备方法,可以有效在共轭骨架外围引入不同烷基链,实现对目标化合物物理性质的调控。二氯甲烷溶液中的紫外–可见吸收光谱表征显示,该类分子在260~600 nm范围有三个最大吸收峰。

A series of organic conjugated small molecules containing heteroatoms (N, S) were designed and synthesized. The different alkyl chains can be introduced through reaction of the lithiated thiophene with corresponding alkyl halide at low temperature. After bromination, the resulting bromo-intermediates can be smoothly converted into corresponding Grignard reagent. Afterwards, the as-prepared Grignard reagents were treated with 1,2,4,5-tetra(S-(pyridine-2’-yl))ben- zenetetrathioate, and then reacted with hydrazine hydrate to afford the target compounds. Upon aforementioned syn-thetic strategy, the physical characters of the target molecules can be fine-tuned by efficient introduction of the different alkyl substituents in the periphery of the conjugated backbone. The UV-Vis absorption spectra of these molecules in dichloromethane solution revealed three maximum absorption peaks between 260 and 600 nm.

何春阳, 薛敏钊, 张帆. 新型含硫氮杂原子有机共轭小分子的合成[J]. 化学工程与技术, 2013, 3(3): 100-104. http://dx.doi.org/10.12677/HJCET.2013.33019


[1] L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, et al. Self-or- ganized discotic liquid crystals for high-efficiency organic pho- tovoltaics. Science, 2001, 293(5532): 1119-1122
[2] F. R. Tverskoy, A. Peters, H. J. Himmel and U. H. F. Bunz. An efficient synthesis of tetraazapentacenes. Angewandte Chemie International Edition, 2011, 50(15): 3557-3560.
[3] Z. Liang, Q. Tang, R. Mao, D. Liu, J. Xu and Q. Miao. The posi- tion of nitrogen in N-heteropentacenes matters. Advanced Mate- rials, 2011, 23(46): 5514-5518.
[4] 王洪宇, 彭波, 韦玮. 含苝酰亚胺衍生物太阳电池材[J]. 化学进展(Progress in Chemistry), 2008, 20(11): 1751-1760.
[5] A. Rao, M. W. B. Wilson, J. M. Hodgkiss, et al. Exciton fission and charge generation via triplet excitons in pentacene/C60 bilay- ers. Journal of the American Chemical Society, 2010, 132(36): 12698-12703.
[6] F. Zhang, D. Wu, Y. Xu, et al. Thiophene-based conjugated oli- gomers for organic solar cells. Journal of Materials Chemistry, 2011, 21(44): 17590-17600.
[7] R. P. Ortiz, J. Casado, V. Hernandez, et al. Thiophene-diazine molecular semiconductors: Synthesis, structural, electrochemical, optical, and electronic structural properties; Implementation in organic field-effect transistors. Chemistry—A European Journal, 2009, 15: 5023-5039.
[8] R. H. L. Kiebooms, P. J. A. Adriaensens, D. J. M. Vanderzande, et al. Grignard reactions on ortho dicarboxylic arene derivatives. Synthesis of 1,3-dithienylisothianaphthene compounds. The Jour- nal of Organic Chemistry, 1997, 62(5): 1473-1480.
[9] C. J. Wharton, R. Wrigglesworth. Synthesis and reactions of 2,3- dihydro-oxazolo[2,3-a]isoindol-5(9bH)-ones. Journal of the Che- mical Society, Perkin Transactions, 1985, 1: 809-813.
[10] A. J. Zucchero, P. L. McGrier and U. H. F. Bunz. Cross-conju- gated cruciform fluorophores. Accounts of Chemical Research, 2009, 43(3): 397-408.
[11] Y. Liu, F. Zhang, C. He, et al. Efficient synthesis and physical properties of novel H-shaped 2,3,7,8-tetraazaanthracene-based conjugated molecules. Chemical Communications, 2012, 48(35): 4166-4168.