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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 240-247
DOI: 10.1055/s-0040-1715564
Short Communication

Synthesis and Characterization of AIE-Active B–N-Coordinated Phenalene Complexes

Yubin Fu 
a   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
,
Junzhi Liu 
b   Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
,
Zhongbin Wu 
c   Department of Materials Science and Engineering, University of Toronto, Toronto, Canada
,
Jan J. Weigand 
d   Chair of Inorganic Molecular Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
,
Xinliang Feng 
a   Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany
› Author Affiliations Funding Information We thank the European Union's Horizon 2020 research and innovation program under grant agreement No. 696656 (Graphene Flagship Core2), ERC Grant on T2DCP, the German Research Foundation (DFG) within the Cluster of Excellence “Center for Advancing Electronics Dresden (cfaed)” and EnhanceNano (No. 391979941) as well as the European Social Fund and the Federal State of Saxony (ESF Project “GRAPHD”, TU Dresden) for financial support. J. Liu is grateful for the startup funding from The University of Hong Kong and the funding support from ITC to the SKL.
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Abstract

Organoboron compounds provide a new line to tune the electronic structures of π-conjugated molecules, which is critical to the development of new organic semiconductor materials. In this work, we demonstrate the synthesis of two novel boron–nitrogen (B−N) coordinated phenalene complexes (BNP-PX and BNP-PA) by employing BN phenalene (BNP) as the acceptor unit and phenoxazine/phenylphenazine groups as the donors. Based on single-crystal X-ray analysis, both BNP-PX and BNP-PA possess highly twisted conformations with the dihedral angles of 76.6 ° and 70.5 °, respectively. The photophysical properties of BNP-PX and BNP-PA are elucidated through UV-vis absorption, fluorescence spectroscopy, and theoretical calculations. In addition, BNP-PX exhibits a large Stokes shift (8,033 cm−1) and excellent aggregated-induced emission behavior. The red organic light-emitting diode device was fabricated based on compound BNP-PX, manifesting its promising application in organic optoelectronic devices.

Key words

donor–acceptor - BN-coordinated compounds - large Stokes shift - AIE effect - OLED device

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1715564.


Supplementary Material



Publication History

Received: 25 March 2020

Accepted: 13 June 2020

Article published online:
30 September 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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