Yellow NIR dye: π-fused bisbenzoBODIPYs with electron-withdrawing groups

Nakamura, Michio; Kitatsuka, Manami; Takahashi, Kohtaro; Nagata, Toshi; Mori, Shigeki; Kuzuhara, Daiki; Okujima, Tetsuo; Yamada, Hiroko; Nakae, Takahiro; Uno, Hidemitsu

doi:10.1039/c3ob41996g

Cited by 36 publications

(5 citation statements)

References 42 publications

(40 reference statements)

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“…A major trend in the development of new, long-wavelength absorbing and emitting dyes relies on the modification of known scaffolds such as cyanines, BODIPY and aza-BODIPY, rhodamines and sila-rhodamines, diketopyrrolopyrroles, etc. ; however, some of these (especially cyanine-based dyes) exhibit poor photostability and/or low fluorescence quantum yields. Within this context, some structural modifications are used to improve the optical characteristics of target molecules, namely: (1) appropriate extension of the π-surface; , (2) rigidification of rotatable moieties; ,, (3) efficient planarization by reducing the dihedral angle between a heterocyclic core and peripheral aromatic units by replacement of phenyl with five-membered heterocyclic rings …”

Section: Introductionmentioning

confidence: 99%

Electron-Rich Dipyrrolonaphthyridinediones: Synthesis and Optical Properties

et al. 2018

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This article describes the design rationale for highly electron-rich dipyrrolonaphthyridinedione (DPND) derivatives bearing substituted amino groups at the 3 and 9 positions, which exhibit absorption in the red and emission in the red/NIR region of the spectrum. These novel dyes are easily synthesized through a two-step protocol consisting of bromination of the DPND molecule followed by Buchwald-Hartwig amination. We demonstrated that the diamino-dipyrrolonaphthyridinediones have high ionization energies (∼4.7 eV) and that the spectroelectrochemical properties can be rationally tuned by altering the nature of the peripheral substituted amino groups. All amino-DPNDs exhibit solvatofluorochromism, which has not been previously reported for dyes possessing this core. Theoretical calculations reveal that in all cases, the strongest absorption is exhibited by the S states which clearly correlate with the HOMO-LUMO orbital transition. As all higher states have lower oscillator strengths, it is clear that fluorescence is completely dominated by the excitation/deexcitation sequence S → S, S → S and that there are no contributions to the fluorescence from excitations to higher states.

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Section: Introductionmentioning

confidence: 99%

Electron-Rich Dipyrrolonaphthyridinediones: Synthesis and Optical Properties

et al. 2018

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“…However, unlike the synthesis of benzo[ b ]-fused BODIPYs, ,, introduction of π-extended conjugation systems at the β,β′-positions is challenging, due to the low reactivity of the unsubstituted 1,7-positions of BODIPYs. , Currently, there are three major synthetic strategies to build [ a ]aryl-fused BODIPYs, as shown in Scheme : (ii) by direct condensation of aryl-fused pyrrole precursors, followed by boron complexation under basic conditions, and (i and iii) via the preparation of BODIPY precursors from cyclohexane-fused pyrroles , or bicyclo[2.2.2]octadiene-fused pyrroles, , followed by DDQ oxidation or retro-Diels–Alder reactions, respectively. However, several disadvantages remain for the above-reported methods: (1) noncommercially available pyrrole precursors require multistep synthesis; (2) the preparation of benzo[ a ]-fused BODIPYs usually suffers from low yields (<10%); , and (3) the aromatization steps usually require strong oxidizing agents ,,, and very high temperatures (>200 °C), , which can easily cause the polymerization or decomposition of BODIPYs. Therefore, new, low-cost, convenient, and easy synthetic methods are required to synthesize [ a ]aryl-fused BODIPYs.…”

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confidence: 82%

Synthesis and Spectroscopic and Cellular Properties of Near-IR [a]Phenanthrene-Fused 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes

et al. 2017

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A new synthetic method to build aryl-fused 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) is reported. The intramolecular cyclization step was completed in a short time (1-2 h) and in high yields (>90%), due to the intrinsic rigid structural conformation of the precursor BODIPY and the high reactivity of its 1,7-bromo groups. The [a]phenanthrene-fused BODIPYs 4a-c were characterized by NMR spectroscopy, HRMS, DFT calculations, and, in the case of 4a, by X-ray crystallography. Spectroscopic studies show that 4a-c strongly absorb and emit in the NIR spectral region, in the range 642-701 nm. In addition, BODIPYs 4b and 4c exhibit no toxicity in the light or dark in HEp2 cells and accumulate intracellularly in a time-dependent manner, mainly in the cell endoplasmic reticulum. These results suggest the potential use of [a]phenanthrene-fused BODIPYs as NIR bioimaging probes.

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“…Because of the rigidity of the structure, these dimers exhibited a small Stokes shift. Fluorophores 151 – 153 and 160 – 165 [100] with similar structures were developed by Uno et al ., and also showed favorable photophysical properties. This study provides novel insights for future research in this area.…”

Section: Photophysical Properties Of Hybrid Fluorophoresmentioning

confidence: 99%

Rational Design and Biological Application of Hybrid Fluorophores

Zhang,

Qu,

Zhang

et al. 2024

Chemistry A European J

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Fluorophores are considered powerful tools for not only enabling the visualization of cell structures, substructures, and biological processes, but also making for the quantitative and qualitative measurement of various analytes in living systems. However, most fluorophores do not meet the diverse requirements for biological applications in terms of their photophysical and biological properties. Hybridization is an important strategy in molecular engineering that provides fluorophores with complementarity and multifunctionality. This review summarizes the basic strategies of hybridization with four classes of fluorophores, including xanthene, cyanine, coumarin, and BODIPY with a focus on their structure‐property relationship (SPR) and biological applications. This review aims to provide rational hybrid ideas for expanding the reservoir of knowledge regarding fluorophores and promoting the development of newly produced fluorophores for applications in the field of life sciences.

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Yellow NIR dye: π-fused bisbenzoBODIPYs with electron-withdrawing groups

Cited by 36 publications

References 42 publications

Electron-Rich Dipyrrolonaphthyridinediones: Synthesis and Optical Properties

Electron-Rich Dipyrrolonaphthyridinediones: Synthesis and Optical Properties

Synthesis and Spectroscopic and Cellular Properties of Near-IR [a]Phenanthrene-Fused 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes

Rational Design and Biological Application of Hybrid Fluorophores

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