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Synlett 2017; 28(16): 2121-2125
DOI: 10.1055/s-0036-1590808
letter
© Georg Thieme Verlag Stuttgart · New York

Tri-Petal Lilac-Like Perylene: Asymmetrical Substituted Platform for Regioselective Ether-Exchange Reaction

Manxi Zhou
a   State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: qflee@mail.buct.edu.cn
,
Lei Zhu
a   State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: qflee@mail.buct.edu.cn
,
Zhimin Sun
a   State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: qflee@mail.buct.edu.cn
,
Zhenqing Yang
b   State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: caodp@mail.buct.edu.cn
,
Dapeng Cao*
b   State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: caodp@mail.buct.edu.cn
,
Qifang Li*
a   State Key Laboratory of Chemical Resource Engineering, College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: qflee@mail.buct.edu.cn
› Author AffiliationsThis research was financially supported by the National Natural Science Foundation of China (No. 51273017, 20974013, 11374070).
Further Information

Publication History

Received: 30 April 2017

Accepted after revision: 28 May 2017

Publication Date:
06 July 2017 (online)

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Abstract

An asymmetrical tri-petal lilac-like platform based on perylene bisimide (PBI) was designed and synthesized to further perform the ether-exchange reaction, while common tetraphenoxy PBI analogue cannot do it. We found that the tri-petal lilac-like platform strategy not only avoids the regioisomers of difunctionalized PBI, but also is a precise and facile way to achieve regioselective introduction of alkyloxy, alkylthio and C=C double bond ended substituents onto the 1-position of perylene bay without the use and removal of the protecting groups. Due to the tunable photoelectrical properties and functional groups at bay position, these n-type PBI derivatives are promising materials for photovoltaic and supramolecular application.

Key words

perylene - asymmetrical - regioselective substitution - acceptor - photovoltaic

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590808.
  • Supporting Information
 

  • References and Notes

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