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The geometrical isomer effect on the structures and photophysical properties of small molecular fluorophores

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Abstract

For the purpose of investigating the geometrical isomer effect on building small organic fluorophores, two geometrical isomers with unsymmetrical D1-A-π-D2 architectures were synthesized: 1-MNPM and 3-MNPM. Single crystal analysis indicated that the two compounds displayed different molecular packing modes, due to the different intermolecular interactions. The frontier molecular orbital analysis indicated that the LUMOs and HOMOs of two compounds were mainly located on the 6-methoxynaphthalene donors. The two compounds showed different emission and absorption behaviors in solid and dilute solution state. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations indicated that during the electron transition process, electrons mainly left the D2 donors and transferred to the acceptor moieties (A). Especially, the D1 donors of two compounds played opposite roles in the electron transition process. The emission behaviors of two compounds in different solvents indicated that they both showed solvatochromism properties and large Stokes shifts.

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Acknowledgements

This work has been supported by Qinglan Project of Jiangsu Province, and National Vocational Education Teacher Teaching innovation Team Construction Project (Project 360A10-04-2019-0017-1/1-72).

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  1. School of Chemical Engineering and Pharmacy, Changzhou Vocational Institute of Engineering, Changzhou, 213164, People’s Republic of China

    Dong-En Wu & Qing-Hui Guo

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  1. Dong-En Wu
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  2. Qing-Hui Guo
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Dong-En Wu contributed to testing, validation, and data curation. Qing-Hui Guo contributed to writing—review, and editing.

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Correspondence to Qing-Hui Guo.

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Wu, DE., Guo, QH. The geometrical isomer effect on the structures and photophysical properties of small molecular fluorophores. Res Chem Intermed 49, 5595–5611 (2023). https://doi.org/10.1007/s11164-023-05111-6

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