Strongly emitting, centrosymmetric, ladder-type bis-coumarins with crankshaft architecture

Kumar, G. Dinesh; Liao, Yu-Chan; Nazir, Rashid; Banasiewicz, Marzena; Chou, Pi-Tai; Gryko, Daniel T.

doi:10.1039/d3cp04121b

Phys. Chem. Chem. Phys.

2023

DOI: 10.1039/d3cp04121b

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Strongly emitting, centrosymmetric, ladder-type bis-coumarins with crankshaft architecture

G. Dinesh Kumar,

Yu-Chan Liao,

Rashid Nazir

et al.

Abstract: Easily accessible, centrosymmetric, crankshaft-shaped bis-coumarins possess strongly bathochromically shifted emission.

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2024

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Cited by 3 publications

References 53 publications

(26 reference statements)

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Benzocoumarin‐Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion

Ueda,

Kuramochi,

Shimizu

et al. 2024

Eur J Org Chem

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Developing aggregation‐induced emission luminogens (AIEgens) is a unique strategy for alleviating concentration quenching of π‐conjugated organic compounds. This AIE behaviour can be induced not only in organic dyes with rotors but also in invertible π‐conjugated systems. Herein, intramolecular Ullmann coupling was used to synthesize π‐twisted triskelion‐shaped AIEgens (2F, 2G, and 2H), in which benzo[f], [g], and [h] coumarins were fused into the benzene core to form a helical propeller shape. These structural isomers had unique molecular thicknesses and planarities depending on the fusion mode of the benzocoumarin. The racemic crystals, PPP and MMM, had different overlapping molecular configurations because of their twisted molecular frameworks. Compounds 2F, 2G and 2H demonstrated weak fluorescence emission in diluted solutions resulting from molecular motions caused by the isomerization process during molecular inversion. By comparison, aggregates exhibited enhanced emission intensity. These π‐twisted triskelions exhibited the characteristics of AIEgens.

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Benzocoumarin‐Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion

Ueda,

Kuramochi,

Shimizu

et al. 2024

Eur J Org Chem

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show abstract

Mechanofluorochromic property of coumarin derivatives containing carbonyl group

Zhang,

Xu,

et al. 2024

Journal of Luminescence

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Amino-containing donor-acceptor biaryls with lactone bridging units as three-state halochromic pi-expanded coumarins

Westlund,

Abdrabbo,

Bruckbauer

et al. 2024

Tetrahedron

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Strongly emitting, centrosymmetric, ladder-type bis-coumarins with crankshaft architecture

Abstract: Easily accessible, centrosymmetric, crankshaft-shaped bis-coumarins possess strongly bathochromically shifted emission.

Cited by 3 publications

References 53 publications

Benzocoumarin‐Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion

Benzocoumarin‐Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion

Mechanofluorochromic property of coumarin derivatives containing carbonyl group

Amino-containing donor-acceptor biaryls with lactone bridging units as three-state halochromic pi-expanded coumarins

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