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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1658 - 1664

DOI: https://doi.org/10.6023/cjoc201912016

Synthesis of Pyrene-Cyclooctatetrathiophene Derivatives and Their Behaviors of Photoluminescence

  • Yang Yujie ,
  • Xu Li ,
  • Wang Hua
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  • a College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004;
    b Research Center for Nanomaterials, Henan University, Kaifeng, Henan 475004

Received date: 2019-12-11

  Revised date: 2020-02-29

  Online published: 2020-03-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672053, 21672054).

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Abstract

Cyclooctatetrathiophene (COTh) is a saddle-typed molecule with the interesting property of aggregation induced emission (AIE) discovered recently. In this paper, pyrene was introduced to the framework of COTh as a luminescent group. Three pyrene-COTh derivatives, mono-pyrene substituted COTh (Py-COTh), tetra-pyrene substituted COTh (4Py-COTh) and tetra(tri(trimethylsilyl)cyclooctatetrathiophenyl)pyrene (12TMS-4COTh-Py) were designed and synthesized. Their absorption spectra, fluorescene emission behaviors in solution, rigid state (77 K) and the aggregation state were explored. On the one hand, with increasing pyrene group to the framework of COTh, the molecular conjugation of pyrene-COTh derivatives, Py-COTh and 4Py-COTh changed slightly, but their emission intensity increased heavily with large red shift in both dilute solution and aggregation state. On the other hand, with the increase of COTh group to the framework of pyrene, the molecular conjugation of pyrene-COTh derivatives, Py-COTh and 12TMS-4COTh-Py changed significantly, and their emission intensity increased remarkably with large red shift in dilute solution. The relationship between the photophysical property and molecular structure is remarkably exhibited in our case.

Key words： cyclooctatetrathiophene; pyrene; synthesis of derivative; absorption spectrum; fluorescence spectrum; aggregation induced emission; structure-activity relationship

Cite this article

Yang Yujie , Xu Li , Wang Hua . Synthesis of Pyrene-Cyclooctatetrathiophene Derivatives and Their Behaviors of Photoluminescence[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1658 -1664 . DOI: 10.6023/cjoc201912016

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