NIR fluorescence of A–D–A type functional dyes modulated by terminal Lewis basic groups

Morimoto, Ami; Hayashi, Yuichiro; Maeda, Takeshi; Yagi, Shigeyuki

doi:10.1016/j.dyepig.2020.108768

Cited by 7 publications

(2 citation statements)

References 48 publications

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“…A-D-A-type dyes, comprising two acceptors and one donor, occasionally manifest distinct photophysical properties compared to their D-A counterparts. 23,24 Since phenothiazine is a strong electron donor and contains two aromatic rings fused through nitrogen and sulfur atoms, we hypothesized that phenothiazine could serve as a valuable donor for constructing A-D-A-type boranil dyes. Furthermore, the butterfly-shaped configuration of the phenothiazine moiety may effectively inhibit intermolecular inter-layer stacking of fluorescent dyes, thereby conferring solid-state fluorescence to these A-D-A-type boranil dyes.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

Luo,

Li,

Wang

et al. 2024

Org. Biomol. Chem.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

Luo,

Li,

Wang

et al. 2024

Org. Biomol. Chem.

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“…Existing NIR scaffolds typically fall in the following three categories, depending on the spatial arrangement pattern of their HOMO–LUMO orbitals: (1) the symmetrical push–pull polymethine dyes with fully overlapping HOMO–LUMO orbitals, e.g., cyanine-type dyes, xanthenoids, BODIPY derivatives, and squaraines; (2) the D-A-D type, the A-D-A type, polymetric −(D–A) n –, or the asymmetric D–A type fluorophores with partially overlapping HOMO/LUMO orbitals; and (3) the X-type fluorophores with crossing HOMO/LUMO orbitals. The fluorescence brightness is evaluated by calculating the product of molar absorptivity and fluorescence quantum yield.…”

Section: Introductionmentioning

confidence: 99%

Stable, Bright, and Long-Fluorescence-Lifetime Dyes for Deep-Near-Infrared Bioimaging

Dong

Wei

et al. 2022

J. Am. Chem. Soc.

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Near-infrared (NIR) fluorophores absorbing maximally in the region beyond 800 nm, i.e., deep-NIR spectral region, are actively sought for biomedical applications. Ideal dyes are bright, nontoxic, photostable, biocompatible, and easily derivatized to introduce functionalities (e.g., for bioconjugation or aqueous solubility). The rational design of such fluorophores remains a major challenge. Silicon-substituted rhodamines have been successful for bioimaging applications in the red spectral region. The longer-wavelength silicon-substituted congeners for the deep-NIR spectral region are unknown to date. We successfully prepared four silicon-substituted bis-benzannulated rhodamine dyes (ESi5a–ESi5d), with an efficient five-step cascade on a gram-scale. Because of the extensive overlapping of their HOMO–LUMO orbitals, ESi5a–ESi5d are highly absorbing (λabs ≈ 865 nm and ε > 105 cm–1 M–1). By restraining both the rotational freedom via annulation and the vibrational freedom via silicon-imparted strain, the fluorochromic scaffold of ESi5 is highly rigid, resulting in an unusually long fluorescence lifetime (τ > 700 ps in CH2Cl2) and a high fluorescence quantum yield (ϕ = 0.14 in CH2Cl2). Their half-lives toward photobleaching are 2 orders of magnitude longer than the current standard (ICG in serum). They are stable in the presence of biorelevant concentration of nucleophiles or reactive oxygen species. They are minimally toxic and readily metabolized. Upon tail vein injection of ESi5a (as an example), the vasculature of a nude mouse was imaged with a high signal-to-background ratio. ESi5 dyes have broad potentials for bioimaging in the deep-NIR spectral region.

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Recent advances in the development of chromic textiles

Abdelrahman¹,

Khattab²

2023

Functional and Technical Textiles

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NIR fluorescence of A–D–A type functional dyes modulated by terminal Lewis basic groups

Cited by 7 publications

References 48 publications

Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

Design, synthesis, and biological application of A–D–A-type boranil fluorescent dyes

Stable, Bright, and Long-Fluorescence-Lifetime Dyes for Deep-Near-Infrared Bioimaging

Recent advances in the development of chromic textiles

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