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BIT Makes Important Progress in the Field of Organic Chiral Luminescent Materials

release date :2020-05-14 01:01:00  |   [ close window ]ViewCount:

  Recently, the research group of Professor Chen Pangkuan  of School of Chemistry and Chemical Engineering, Beijing Institute of Technology(BIT) has made important progress in the research of organic chiral luminescent materials, publishing a paper entitled "Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar [5] arenes with Boron Chemistry" in cooperation with Professor Wang Suning  on the top international journal of chemistry ANGEW(Angew. Chem. Int. Ed. 2020, DOI: 10.1002/anie.202001145). The first author of this work is  Chen Jinfa , a 2018 doctoral student of School of Chemistry and Chemical Engineering.

  Circularly polarized luminescence (CPL) refers a property, that a chiral luminescence system can emit circularly polarized light.  It can not only intuitively reflect the excited state structure information of the chiral luminescence system, but also has wide application prospects in the fields of CPL optical display, information storage, bioprobe, CPL laser and so on. Circularly polarized luminescence is inseparable from the design and synthesis of chiral structural materials, but for a long time, the researches about CPL materials have been focused on chiral rare earth complexes and small organic molecules (binadiene, spiroene), researches on CPL chiral macrocyclic compounds are rarely reported. 

Figure 1 Schematic diagram of molecular design strategy

  Pillar arene is a typical representative of the main body of supramolecular macrocycles of a new generation, which is widely used in supramolecular assembly and host-guest chemistry. Recently, a highly elastic self repairing biomimetic polymer gel material (ACS Appl. Polym. Mater. 2019, 1, 2224) has been reported by the same author.  Generally, a pair of stereoisomers of the pillar arene lose their optical rotation due to the rapid turnover of aromatic rings, so how to effectively prevent their racemization has become the focus of attention in the field. In 2019, the research group found that the aggregation state can effectively inhibit the rotation of the benzene ring to improve the luminescent efficiency (J. Mater. Chem. C 2019, 7, 11747), but it was still difficult to obtain optically pure enantiomers. Based on the long-term research of organoboron, the research group use the unique luminescent properties and spatial structure of triarylboron and triphenylamine to combine organoboron chemistry with pillar arene for the first time, preparing an axially conjugated pillar arene derivative (P5BN). The significant spatial effect of triphenylamine (Donor) and triarylboron (Acceptor) effectively inhibits the inversion of the aromatic ring, enabling the enantiomer to obtain an efficient chiral resolution. We first reported the circularly polarized luminescent materials based on the pillar arene.  Moreover, the charge transfer within the molecule endows the material with unique temperature response property, which is a potential low-temperature fluorescence probe.  This work not only has considerable application prospects in the recognition direction of chiral small molecules, but also greatly promotes the development of chiral CPL macrocyclic materials.

Figure 2 (a) Spectrum of P5BN in solid-state CPL; (b) Fluorescence discoloration phenomenon of P5BN in thermal response.

  Paper Details: Jin-Fa Chen, Xiaodong Yin, Bowen Wang, Kai Zhang, Guoyun Meng, Songhe Zhang, Yafei Shi, Nan Wang, Suning Wang & Pangkuan Chen*. Planar Chiral Organoboranes with Thermoresponsive Emission and Circularly Polarized Luminescence: Integration of Pillar[5]arenes with Boron Chemistry. Angewandte Chemie International Edtion, doi: 10.1002/anie.202001145.

  Paper Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.202001145

 

Brief Introduction of the Author:

  Chen Puangkuan, professor and doctoral tutor of School of Chemistry and Chemical Engineering, BIT, was selected into the National Overseas High-level Talent Introduction Program Youth Project. He has long been devoted to the research work of new luminescent materials and intelligent sensing materials, and has accumulated a large amount of experience especially in the fields of controllable synthesis of organoboron conjugated molecules, photoelectric performance control and so on. At the same time, his research in the emerging "dynamic chemistry" field is distinctive, exploring initially  the bionic properties (such as mechanical force response, signal memory, damage repair, etc.) of super (high) molecular gels and related materials. He has undertaken general projects of the National Natural Science Foundation of China and published more than thirty SCI papers, including J. Am. Chem. Soc, Angew. Chem., Chem. Sci. and so on. A number of his works have been specially reported by portal websites for over twenty times, including C & E news, JACS spotlights, JACS selections, Angewandte highlights and so on. 

 

Editor: News Agency of BIT
Translator: News Agency of BIT, Lirui Liu

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