ChemInform Abstract: Influence of the N‐Substituent on the Photophysical Properties of Oxacarbocyanines in Solution.

Pevenage, Dimitri; Corens, David; Dehaen, Wim; Auweraer, Mark Van der; Schryver, F. C. De

doi:10.1002/chin.199812153

Cited by 11 publications

(27 citation statements)

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“…Only a small hypsochromic shift of about 186 cm À1 (5 nm) is present in the absorption maxima on going from toluene to THF and could be attributed to the combined result of the different solvent polarizability (n toluene = 1.49, n THF = 1.40) and/or the decrease of the dipole moment in the excited state S 1 with respect to the ground state S 0 . This shift is consistent with the general behavior of other BODIPY derivatives, [26][27][28] cyanine dyes 29,30 and aromatic amines. 31 The emission spectra closely resemble the mirror image of the corresponding S 0 -S 1 transition showing a relative small Stokes shift, due to the rigidity of the BODIPY chromophore in BODIPY 2Cl, BODIPY 2O, BODIPY 2S and BODIPY 2Se.…”

Section: Steady State Measurementssupporting

confidence: 88%

Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

et al. 2009

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Section: Steady State Measurementssupporting

confidence: 88%

Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

et al. 2009

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“…For 6 , there is also a good correlation between y = ν̃ em and n 2 ( r = 0.905) or the Bayliss function [ f ( n 2 ) = ( n 2 – 1)/(2 n 2 + 1)] ( r = 0.899). This is additional evidence that van der Waals and excitonic interactions with a polarizable solvent are primarily responsible for the experimentally observed solvent‐dependent shifts of ν̃ em …”

Section: Resultsmentioning

confidence: 57%

Synthesis and Spectroscopy of Benzylamine‐Substituted BODIPYs for Bioimaging

et al. 2018

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Three new boron dipyrromethene (BODIPY) dyes substituted with a benzylamino group at the 3‐position have been synthesized from halogenated BODIPYs by nucleophilic substitution. The spectroscopic and photophysical properties have been explored in different solvents and have been compared with an analogous 8‐benzylaminoBODIPY derivative. The position of the benzylamino group has a significant influence on the spectral band positions, fluorescence quantum yields, and fluorescence lifetimes. The 8‐benzylaminoBODIPY emits in the blue range, whereas the 3‐substituted shows green fluorescence. Additionally, the extension of the conjugation at the 5‐position of 3‐benzylaminoBODIPY produces a bathochromic shift of the absorption and emission spectra. The effect of solvents on their spectroscopic features has been investigated using the generalized Catalán solvent scales. Quantum‐chemical calculations have been performed to assess the effect of the position of the substitution on the spectroscopic properties. Finally, the BODIPY dyes have been employed as probes in fluorescence lifetime imaging of living cells, demonstrating their high potential for bioimaging.

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“…39 The slopes of the plots of ν j abs [(-4.7 ( 0.5) × 10 3 cm -1 ] and ν j em [(-4.2 ( 0.5) × 10 3 cm -1 ] versus f(n 2 ) are similar. This agrees with our assumption that the Franck-Condon excited state and the relaxed, fluorescent excited state are virtually identical: they have the same oscillator strength and nearly the same energy.…”

Section: Resultsmentioning

confidence: 83%

3,5-Dianilino Substituted Difluoroboron Dipyrromethene: Synthesis, Spectroscopy, Photophysics, Crystal Structure, Electrochemistry, and Quantum-Chemical Calculations

et al. 2009

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4,4-Difluoro-3,5-bis(phenylamino)-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene (1), a symmetric fluorescent difluoroboron dipyrromethene dye, has been synthesized by nucleophilic substitution of 3,5-dichloro-4,4-difluoro-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene with aniline. The solvent-dependent spectroscopic and photophysical properties have been investigated by means of UV-vis spectrophotometry and steady-state and time-resolved fluorometry and are compared to those of the nonsymmetrically substituted 5-chloro-4,4-difluoro-3-phenylamino-8-(4-tolyl)-4-bora-3a,4a-diaza-s-indacene (2). A new, generalized treatment of the solvent effect, proposed by Catalán (J. Phys. Chem. B 2009, 113, 5951-5960) and based on a set of four mutually independent, empirical scales (dipolarity, polarizability, acidity, and basicity of the medium) is the most appropriate for describing the solvatochromic shifts of the UV-vis absorption and fluorescence emission of 1 and 2. In contrast to the nonsymmetric compound 2, the symmetric dye 1 has higher fluorescence quantum yields (0.45-0.86) and longer fluorescence lifetimes (3.36-4.03 ns) in all solvents studied and its emission maxima are shifted bathochromically by ∼45 nm. Large differences are also evident in the redox electrochemistry of the two dyes, with the symmetric analogue 1 possessing a much lower oxidation potential (∼600 mV) than the nonsymmetric 2. The absorption bandwidths and Stokes shifts of symmetric 1 are much smaller than those for nonsymmetric 2. For both dyes, the value of the fluorescence rate constant, [k f ) (1.7 ( 0.3) × 10 8 s], does not depend much on the solvent tested. X-ray diffraction analysis of 1 shows that the BODIPY core possesses a planar structure. Quantum-chemical calculations support the different photophysical behavior of the symmetric derivative 1 vis-à-vis the nonsymmetric 2.

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ChemInform Abstract: Influence of the N‐Substituent on the Photophysical Properties of Oxacarbocyanines in Solution.

Cited by 11 publications

References 0 publications

Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

Synthesis and photophysical characterization of chalcogen substituted BODIPY dyes

Synthesis and Spectroscopy of Benzylamine‐Substituted BODIPYs for Bioimaging

3,5-Dianilino Substituted Difluoroboron Dipyrromethene: Synthesis, Spectroscopy, Photophysics, Crystal Structure, Electrochemistry, and Quantum-Chemical Calculations

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