Sequential Multistep Excited‐State Structural Transformations in N,N′‐Diphenyl‐dihydrodibenzophenazine Fluorophores

We demonstrate that a single polycyclic π‐scaffold can undergo sequential multistep excited‐state structural evolution along the bent, planar, and twisted conformers, which coexist to produce intrinsic multiple fluorescence emissions in room‐temperature solution. By installing a methyl or trifluorom...

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Published in:Angewandte Chemie International Edition 2023-07, Vol.62 (29)
Main Authors: Jin, Xin, Guo, Shiyan, Wang, Xueli, Cong, Muyu, Chen, Jinquan, Zhang, Zhiyun, Su, Jianhua, Da‐Hui Qu, He, Tian
Format: Article
Language:English
Subjects:
Broadband
Chemical compounds
Emissions
Evolution
Fluorescence
Fluorophores
Molecular weight
Potential energy
Spectroscopy
Steric effects
Steric hindrance
Substitutes
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container_title Angewandte Chemie International Edition
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Guo, Shiyan
Wang, Xueli
Cong, Muyu
Chen, Jinquan
Zhang, Zhiyun
Su, Jianhua
Da‐Hui Qu
He, Tian
description We demonstrate that a single polycyclic π‐scaffold can undergo sequential multistep excited‐state structural evolution along the bent, planar, and twisted conformers, which coexist to produce intrinsic multiple fluorescence emissions in room‐temperature solution. By installing a methyl or trifluoromethyl group on the ortho‐site of N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine (DPAC), the enhanced steric effects change the fluorescence emission of DPAC from a dominant red band to well‐resolved triple bands. The ultra‐broadband triple emissions of ortho‐substituted DPACs range from ≈350 to ≈850 nm, which is unprecedented for small fluorophores with molecular weight of
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By installing a methyl or trifluoromethyl group on the ortho‐site of N,N′‐diphenyl‐dihydrodibenzo[a,c]phenazine (DPAC), the enhanced steric effects change the fluorescence emission of DPAC from a dominant red band to well‐resolved triple bands. The ultra‐broadband triple emissions of ortho‐substituted DPACs range from ≈350 to ≈850 nm, which is unprecedented for small fluorophores with molecular weight of &lt;500. Ultrafast spectroscopy and theoretical calculations clearly reveal that the above dramatic changes originate from the influence of steric hindrance on the shape of excited state potential energy surface (S1 PES). Compared to the steep S1 PES of parental DPAC, the introduction of ortho‐substituent is shown to make the path of structural evolution in S1 wider and flatter, so the ortho‐substituted derivatives exhibit slower structural transformations from bent to planar and then to twisted forms, yielding intrinsic triple emission. 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subjects Broadband
Chemical compounds
Emissions
Evolution
Fluorescence
Fluorophores
Molecular weight
Potential energy
Spectroscopy
Steric effects
Steric hindrance
Substitutes
title Sequential Multistep Excited‐State Structural Transformations in N,N′‐Diphenyl‐dihydrodibenzophenazine Fluorophores
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