Halogen-substituent effect on the spectroscopic properties of 2-phenyl-6-dimethylaminobenzothiazoles

Misawa, Rena; Matsuhashi, Chihiro; Yamaji, Minoru; Mutai, Toshiki; Yoshikawa, Isao; Houjou, Hirohiko; Noguchi, Keiichi; Maki, Shôjirô; Hirano, Takashi

doi:10.1016/j.tetlet.2019.05.052

Cited by 6 publications

(1 citation statement)

References 12 publications

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“…The integration of Cl disrupted slipped π-stacking but heavy atom halogen substitution reduced the fluorescence efficiency as well as blue shifted the fluorescence. [55][56][57] Density functional theoretical (DFT) studies were performed to gain insight into the electron density distribution and charge transfer (Fig. 3b).…”

Section: Resultsmentioning

confidence: 99%

Anthracene–naphthylacetonitrile fluorescent isomers and Cl/H substituent dependent molecular packing, solid-state fluorescence and mechanofluorochromism

Ravi,

Priyadharshini,

Karthikeyan

et al. 2023

CrystEngComm

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Section: Resultsmentioning

confidence: 99%

Anthracene–naphthylacetonitrile fluorescent isomers and Cl/H substituent dependent molecular packing, solid-state fluorescence and mechanofluorochromism

Ravi,

Priyadharshini,

Karthikeyan

et al. 2023

CrystEngComm

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Influence of Halogen Substituents on the Photophysical Properties of 7‐Hydroxycoumarin: Insights from Experimental and Theoretical Studies

Hawkins,

Adair,

Ryder

et al. 2024

ChemPhysChem

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Benzopyrone is a popular fluorescent scaffold, but how chemical modifications affect its properties is less understood. We investigated this using halogenated 7‐hydroxycoumarin, unsubstituted 4‐methylumbiliferone, and ortho‐chloro and bromo substitutions on the phenolic ring. Experimental charge density data and computational methods revealed that halogenation at the ortho position significantly reduced quantum yield (QY). Specifically, 7‐hydroxycoumarin (1) had a QY of 70%, while ortho‐chloro (2) and ortho‐bromo (3) had QYs of 61% and 30%, respectively. Experimental data showed that all probes excited similarly, but the electrostatic potential and dipole moments indicated that 2 and 3 dissipated excitation energy more easily due to charge separation. The heavy‐atom effect of Cl and Br did not fully explain the QY reductions, suggesting other radiative decay processes were involved. By incorporating spin‐orbit coupling (SOC) effects, we estimated intersystem crossing (ISC) and phosphorescence rates, providing theoretical QYs of 78% for 1, 59% for 2, and 15% for 3. The large deviation for 3 was attributed to its higher SOC potential. Our findings indicate that 3’s reduced QY results from a mix of SOC‐induced ISC and charge dissipation, while 2’s reduction is primarily due to charge separation. Further studies are needed to validate this approach with other scaffolds.

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The effect of ligand modification on the structure and electronic spectra of tetraazamacrocyclic complexes Au(III)

Kryuchkova

Миронов

Afanas’eva

2021

Journal of Molecular Structure

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Halogen-substituent effect on the spectroscopic properties of 2-phenyl-6-dimethylaminobenzothiazoles

Cited by 6 publications

References 12 publications

Anthracene–naphthylacetonitrile fluorescent isomers and Cl/H substituent dependent molecular packing, solid-state fluorescence and mechanofluorochromism

Anthracene–naphthylacetonitrile fluorescent isomers and Cl/H substituent dependent molecular packing, solid-state fluorescence and mechanofluorochromism

Influence of Halogen Substituents on the Photophysical Properties of 7‐Hydroxycoumarin: Insights from Experimental and Theoretical Studies

The effect of ligand modification on the structure and electronic spectra of tetraazamacrocyclic complexes Au(III)

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