A Novel Approach to the Structural Design of Dual-State Emission Luminogens by Combining Tetraphenylethylene with Anthracene via Dihydroisoxazole

被引:0
作者
Lu, Wenjun [1 ]
Zhao, Yingyi [1 ]
Sun, Baiwang [1 ]
机构
[1] Southeast Univ, Sch Chem & Chem Engn, Nanjing 211189, Peoples R China
来源
CHEMPHOTOCHEM | 2024年 / 8卷 / 11期
基金
中国国家自然科学基金;
关键词
anthracene; dihydroisoxazole; Dual-state emission; tetraphenylethylene; AGGREGATION-INDUCED EMISSION;
D O I
10.1002/cptc.202400009
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Dual-state emission luminescent materials (DSEgens), which exhibit bright emissions in boththe solid state and solution, have been attracting research interest in the design of multifunctional materials.The delicate manipulation of molecular structures remains challenging in the synthesis of DSEgens. In this article, two novel molecules with dual-state emission were synthesized by combining tetraphenylethylene with anthracene via dihydroisoxazole. Tetraphenylethylene acts as a solid-state emitter, while the anthracene core functions as an emitter in the solution state to achieve DSE fluorescence properties. The THF/DCM mixture resulted in successfully obtaining the crystal structures of TPE-An-H and TPE-An-Cl. The quantum yields (QYs) of TPE-An-H were 31 % and 42 % in EA and the solid state, respectively, while TPE-An-Cl exhibited QYs of 32 % and 34 %. The novel synthesis method in this paper combines AIE with ACQ via dihydroisoxazole to achieve dual-state emission, offering a new and concise approach. Tetraphenylethylene and anthracene molecules are connected by a single bond while maintaining their respective fluorescence properties. Tetraphenylethylene acts as a solid-state emitter, while the anthracene core functions as an emitter in the solution state to achieve DSE fluorescence properties. A novel approach to the structural design of dual-state emission luminogens, which combines AIE with ACQ via dihydroisoxazole. image
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页数:9
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共 54 条
[1]   Near-IR organic sensitizers containing squaraine and phenothiazine units for dye-sensitized solar cells [J].
Bae, Seong Hee ;
Seo, Kang Deuk ;
Choi, Won Seok ;
Hong, Ji Yeoun ;
Kim, Hwan Kyu .
DYES AND PIGMENTS, 2015, 113 :18-26
[2]   Dual-State Emission (DSE) in Organic Fluorophores: Design and Applications [J].
Belmonte-Vazquez, Jose L. ;
Amador-Sanchez, Yoarhy A. ;
Rodriguez-Cortes, Lizbeth A. ;
Rodriguez-Molina, Braulio .
CHEMISTRY OF MATERIALS, 2021, 33 (18) :7160-7184
[3]   Solid-state emitting twisted π-conjugate as AIE-active DSE-gen: in vitro anticancer properties against FaDu and 4T1 with biocompatibility and bioimaging [J].
Bhuin, Shouvik ;
Sharma, Pravesh ;
Chakraborty, Purbali ;
Kulkarni, Onkar Prakash ;
Chakravarty, Manab .
JOURNAL OF MATERIALS CHEMISTRY B, 2022, 11 (01) :188-203
[4]   Dual-State Emission and Two-Photon Absorption Tuned by Benzonitrile Substitution in 2,3,4,5-Tetraphenyl-1H-Pyrrole [J].
Cesaretti, Alessio ;
Cai, Zhengxu ;
Kim, Junseok ;
Kim, Hyungjun ;
Lei, Yunxiang ;
Carlotti, Benedetta .
CHEMPHOTOCHEM, 2023, 7 (06)
[5]   Organic Resistive Memory Devices: Performance Enhancement, Integration, and Advanced Architectures [J].
Cho, Byungjin ;
Song, Sunghun ;
Ji, Yongsung ;
Kim, Tae-Wook ;
Lee, Takhee .
ADVANCED FUNCTIONAL MATERIALS, 2011, 21 (15) :2806-2829
[6]   Effect of Substituent Position on the Photophysical Properties of Triphenylpyrrole Isomers [J].
Dong, Lichao ;
Shang, Guojun ;
Shi, Jianbing ;
Zhi, Junge ;
Tong, Bin ;
Dong, Yuping .
JOURNAL OF PHYSICAL CHEMISTRY C, 2017, 121 (21) :11658-11664
[7]   Tetraphenylethene 9,10-Diphenylanthracene Derivatives - Synthesis and Photophysical Properties [J].
Gao, Can ;
Seow, Jia Yi ;
Zhang, Bolong ;
Hall, Christopher R. ;
Tilley, Andrew J. ;
White, Jonathan M. ;
Smith, Trevor A. ;
Wong, Wallace W. H. .
CHEMPLUSCHEM, 2019, 84 (06) :746-753
[8]   Catalytic Rearrangement of Aldoximes to Primary Amides in Environmentally Friendly Media under Thermal and Microwave Heating: Another Application of the Bis(allyl)-Ruthenium(IV) Dimer [{RuCl(μ-Cl)(η3:η3-C10H16)}2] [J].
Gonzalez-Liste, Pedro J. ;
Cadierno, Victorio ;
Garcia-Garrido, Sergio E. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2015, 3 (11) :3004-3011
[9]   High-Density DNA Functionalization by a Combination of Cu-Catalyzed and Cu-Free Click Chemistry [J].
Gutsmiedl, Katrin ;
Fazio, Danila ;
Carell, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (23) :6877-6883
[10]   Effect of TEMPO-oxidization and rapid cooling on thermo-structural properties of nanocellulose [J].
Haniffa, Mhd Abd Cader Mhd ;
Ching, Yern Chee ;
Chuah, Cheng Hock ;
Ching, Kuan Yong ;
Nazri, Nik ;
Abdullah, Luqman Chuah ;
Nai-Shang, Liou .
CARBOHYDRATE POLYMERS, 2017, 173 :91-99