Progress in Synthesis and Aggregation-Induced Phosphorescence of Persulfurated Arene Compounds

doi:10.6023/cjoc202204063

Abstract

Aggregation-induced emission (AIE) has received extensive attention in the field of optical materials since its discovery. Organic phosphorescence with high efficiency and long lifetime exhibits excellent luminescent properties and high flexibility of modification, which is an important development direction of organic light-emitting materials in the future. Persulfurated arenes as a typical class of aggregation-induced phosphorescence (AIP) materials possess highly twistable molecular structures and abundant modification sites. Therefore, a number of luminescent systems (such as solution state, thin film state, crystalline state, etc.) based on these compounds have been developed. At the same time, persulfurated arene exhibit a unique molecular conformation transition in the excited state, which not only provides a theoretical basis for the regulation of molecular self-assembly morphology and luminescence properties under in situ photocontrol, but also builds a fabulous platform for developing abundant luminescence systems. This paper aims to summarize the aggregation induced phosphorescence properties of different series of persulfurated arenes under various regulation modes. Combined with the research practice of our research group in this field, the AIP properties of persulfurated arenes in recent years are reviewed. The possible problems in the current research are briefly prospected, hoping to provide some reference and thinking for the future development direction of AIP materials.

Key words: aggregation induced emission, persulfurated arenes, phosphorescence, light control, stimulus responsiveness

Cite this article

Yunle Lu, Yanjie Wang, Liangliang Zhu, Bingbing Yue. Progress in Synthesis and Aggregation-Induced Phosphorescence of Persulfurated Arene Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3549-3561.

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Fig. & Tab. 17

Figure 1. Chemical structure of multi-substitued (persulfurated) arenes

Figure 2. Synthesis and structure of Two-sulfurated and four- sulfurated aromatic compounds

Figure 3. First synthesis of hexakis(phenylthio)benzene

Figure 4. Reaction conditions of nucleophilic substitution for persulfurated benzene molecules

Figure 5. Synthesis of carboxyl-substitued persulfurated arenes(Ast_6COOH, Ast_4COOH and Ast_2COOH).

Figure 6. Strong green phosphorescence formed by self-assembly of Ast_6COO－ in water with Pb2＋

Figure 7. AIP of AS(CN)T_4COO－ triggered by coordination with Ca2＋

Figure 8. Photo-induced AIP process of Ast_6COO－

Figure 9. Illustration of photoinduced organic-phase AIE

Figure 10. Tunable fluorescence-phosphorescence complex emission of Ast_6NHCOCH3

Figure 11. Supramoleular chiral switch between fluorescence and phosphorescence induced by helical self-assemble

Figure 12. Sol-gel platform with a combination of AIE, RTP, CPL properties constructed by HTB-D/LG gelator

Figure 13. Persulfurated arene compounds syntheised by Ceroni group

Figure 14. Persulfurated arenes exhibiting properties of ion sensing

Figure 15. Multi-color luminescence properties of AST_6BN and AST_6OH under different stimuli

Figure 16. Manipulating crystals through photophysical method realized by photoexcitation-induced molecular realignment

Figure 17. Chemical structure of Na_8 and Na_8CH3 and schematic illustration of emission induced by CH-π interaction

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