Rational design of systematic AIEEgens further modified by substituents from a novel chain structure
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tional design of systematic AIEEgens further modified by substituents from a novel chain structure 1
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Hao Lu , Kun Wang , Beibei Liu , Meng Wang , Mingming Huang , Yue Zhang & 1* Jiping Yang 1
Key Laboratory of Aerospace Advanced Materials and Performance, Ministry of Education, School of Materials Science and Engineering, 2
Beihang University, Beijing 100191, China; State Key Laboratory of Advanced Power Transmission Technology, State Grid Global Energy Interconnection Research Institute, Beijing 102211, China
Received June 2, 2020; accepted July 16, 2020; published online September 15, 2020
The expansion of new structures in aggregation-induced emission/aggregation-induced emission enhancement (AIE/AIEE) systems has attracted persistent attention recently, from which more luminescent functional molecules with characteristic skeletons are derived to satisfy specialized applications. In this study, a series of derivatives cored by tetraphenyl enamine with various terminal groups were designed and synthesized based on a novel p-π conjugate chain structure (–C=C–N–). Experimental and theoretical studies reveal that attaching modified groups to enamine core is decisive to achieve successful conversion from non-luminance to AIEE-activity. Moreover, due to different substituent effect on electronic structure, molecular conformation and molecular packing, diverse enamine compounds exhibited prominent substituent tunable emission properties, realizing regulated AIEE effect and multicolor emitting. These results not only offer a new method to design AIEgens/AIEEgens with p-π conjugate chain structures, but also provide in-depth knowledge for functional modifications of more novel AIE/AIEE units and materials. aggregation-induced emission enhancement, chain structure, enamine derivatives, substituent tunable emission Citation:
Lu H, Wang K, Liu B, Wang M, Huang M, Zhang Y, Yang J. Rational design of systematic AIEEgens further modified by substituents from a novel chain structure. Sci China Chem, 2020, 63, https://doi.org/10.1007/s11426-020-9831-y
1 Introduction Aggregation-induced emission/aggregation-induced emission enhancement luminogens (AIEgens/AIEEgens), initially proposed and investigated by Tang et al. in 2001, are of great significance due to their wide applications in chemosensors, bio-imaging, optoelectronics [1–9], etc. So far, hundreds of compounds have been exploited to exhibit AIE/ AIEE properties. Based on the primary characteristic of molecular structures, they can be divided into the following categories as pure hydrocarbon aromatics, organic heteroa*Corresponding author (email: [email protected])
tom molecules and clusterization-triggered luminophores [10–12]. Among these types of AIEgens/AIEEgens, organic luminescent molecules with conjugate chain structures are regarded as a crucial constitution. Generally, most AIE/AIEE luminogens feature propeller-like configuration with several rotors attaching to a stator, which are obedient to the most accepted AIE/AIEE mechanism, namely as the
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