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Molecular Crystals and Liquid Crystals Volume 764, 2023 - Issue 1
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Research Article

Anthracene-bridged diarylamine isomers with identical amine–amine distances: Syntheses, (spectro)electrochemistry and theoretical calculations

Jingwen Xua College of Chemistry and Material Science, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Hengyang Normal University, Hengyang, Hunan, P. R. China;b Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hengyang, Hunan, P. R. China;c Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the upper Reaches of Xiangjiang River, Hengyang, Hunan, P. R. ChinaView further author information
,
Wenbo Xiaoa College of Chemistry and Material Science, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Hengyang Normal University, Hengyang, Hunan, P. R. China;b Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hengyang, Hunan, P. R. China;c Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the upper Reaches of Xiangjiang River, Hengyang, Hunan, P. R. ChinaView further author information
,
Yonglin Xiaa College of Chemistry and Material Science, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Hengyang Normal University, Hengyang, Hunan, P. R. China;b Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hengyang, Hunan, P. R. China;c Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the upper Reaches of Xiangjiang River, Hengyang, Hunan, P. R. ChinaView further author information
,
Lingyun Yea College of Chemistry and Material Science, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Hengyang Normal University, Hengyang, Hunan, P. R. China;b Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hengyang, Hunan, P. R. China;c Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the upper Reaches of Xiangjiang River, Hengyang, Hunan, P. R. ChinaView further author information
,
Yuanyang Luoa College of Chemistry and Material Science, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Hengyang Normal University, Hengyang, Hunan, P. R. China;b Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hengyang, Hunan, P. R. China;c Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the upper Reaches of Xiangjiang River, Hengyang, Hunan, P. R. ChinaView further author information
&
Ya-Ping Oua College of Chemistry and Material Science, Hunan Provincial Key Laboratory of Functional Metal-Organic Compounds, Hengyang Normal University, Hengyang, Hunan, P. R. China;b Key Laboratory of Organometallic New Materials (Hengyang Normal University), College of Hunan Province, Hengyang, Hunan, P. R. China;c Hunan Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the upper Reaches of Xiangjiang River, Hengyang, Hunan, P. R. ChinaCorrespondence[email protected]
View further author information
Pages 103-114 | Published online: 27 Apr 2023
 
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Abstract

Two athracene-bridged diarylamine isomers 1 and 2 were constructed and fully characterized. The electrochemical results showed that ΔE of compound 2 was significantly higher than that of 1, which indicated that the mixed-valence compound 2+ had higher thermodynamic stability than 1+. Spectroelectrochemistry reflected that the NIR absorption of 2+ exhibited a significant blue shift compared with reported compound 1+. The calculated electronic coupling constant and spin density distribution indicated that 2+ had larger charge delocalization than 1+ under the identical amine-amine distances. The TDDFT predicted β-HOSO→β-LUSO transition from 2+ which further confirmed the existence of N→N·+ IVCT transition.

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Funding

The authors acknowledge the financial support from National Natural Science Foundation of China (21602049), the Natural Science Foundation of Hunan Province, China (Nos. 2021JJ30058, 2017JJ3004), Scientific Research Projects of Education Department of Hunan Province (No. 21A0441), the Science and Technology Bureau of Hengyang, China (No. 2019jh010912), the Aid Programs for Technology Innovative Team, Key Discipline in Education Department of Hunan Province and Functional Metal-Organic Compounds of Hunan Science and Technology Innovation Team, and the Support Plan for Talents in Hengyang Normal University.

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