Series of polymethine dyes derived from 2,2-difluoro-1,3,2-(2H)-dioxaborine of 3-acetyl-7-diethylamino-4-hydroxycoumarin

Gerasov, Andriy O.; Shandura, Mykola P.; Kovtun, Yu. P.

doi:10.1016/j.dyepig.2007.08.013

Cited by 48 publications

(35 citation statements)

References 18 publications

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“…Comparing the data of Table 2 with the previously reported spectroscopic evidence [8], it is clear that fused dioxaborine dyes containing two dialkylamino groups on the coumarin moiety somewhat differ in spectral properties from their mono-substituted analogues (Fig. 3).…”

Section: Resultsmentioning

confidence: 78%

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Polymethine dyes derived from the boron difluoride complex of 3-acetyl-5,7-di(pyrrolidin-1-yl)-4-hydroxycoumarin

2008

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Section: Resultsmentioning

confidence: 78%

“…To prevent hydrolytic cleavage of the dioxaborine ring, we previously proposed to introduce a dialkylamino group into the coumarin moiety (as in structure B, Fig. 1) [8]. As also shown, this structural modification not only makes the dyes more resistant to hydrolysis but also gives rise to significant spectral effects.…”

Section: Introductionmentioning

confidence: 93%

Polymethine dyes derived from the boron difluoride complex of 3-acetyl-5,7-di(pyrrolidin-1-yl)-4-hydroxycoumarin

2008

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“…The similar spectral effect was observed for the dioxaborine dyes based on coumarine nuclei. For instance, in the acetonitrile solution of the dye 12 with unsubstituted coumarine nuclei = 0.2% whereas the quantum yield increases to 11% with the introduction of the electron donating diethylamino group (dye 13) [12]. Therefore, the boron difluoride complexes of the merocyanines based on dehydroacetic acid were found to be sensitive fluorescence indicators for primary and secondary aliphatic amines.…”

Section: Methodsmentioning

confidence: 96%

“…It is well-known, that structural analogs of dehydroacetic acid -4-hydroxy-3-acetylcumarines easily form boron difluoride complexes which can provide intense and deep colored polymethine dyes with high ability to fluorescence [11,12]. Moreover, the interest to none-linear optical properties (NLO) of 2,2-difluoro-1,3,2-(2H)-dioxaborine dyes, recently tends to increase [13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

1,3,2‐(2H)‐dioxaborine polymethine dyes on the base of dehydroacetic acid — effective fluorescent amine probes

Gerasov

Shandura

Kovtun

et al. 2008

Journal of Heterocyclic Chem

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A number of new polymethine dyes based on the boron difluoride complexes of dehydroacetic acid and 3‐acetyl‐4‐hydroxypyridone has been synthesized. Their spectral‐luminescent properties have been investigated. The reaction of obtained merocyanines with primary and secondary amines has been studied. These low fluorescent dyes gave highly fluorescent open chain products, which on further heating cyclized to weakly fluorescent pyridone dyes.

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“…Fluorescence quantum yields (Φ) for compounds 4 and 7 were determined relative to Rhodamine 6G (Φ = 0.95, EtOH), whereas for compounds 11, 12a, 13, and 14 they were determined relative to pentamethinedioxaborinate (Φ = 0.57, CH 2 Cl 2 ). [15] …”

Section: Methodsmentioning

confidence: 97%

Boradipyrromethenecyanines

2009

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A series of meso-polymethine-substituted BODIPY compounds have been synthesized by the reaction of mesomethyl-3,5-diphenylboradipyrromethene with a number of hemicyanine derivatives. The dyes obtained exhibit intense long-wavelength absorption, but weak fluorescence. Upon protonation of the dyes the long-wavelength band disappears and the intensity of the short-wavelength band in- IntroductionBoradipyrromethene dyes (4,4-difluoro-4-bora-3a,4a-diazas-indacenes, BODIPY, BDP) have attracted considerable attention over the past two decades. The ever increasing interest in this type of compound is due to their excellent thermal, chemical, and photochemical stability, high molar absorptivity, high fluorescence quantum yields, insensitivity to solvent polarity and pH, long excited-state lifetimes, a large two-photon cross-section for multiphoton excitation, lack of ionic charge, and good solubility.[1] However, the absorption maxima of the majority of BODIPYs are below 600 nm. Long-wavelength dyes are important for both basic and applied research [2] and therefore many synthetic approaches exist for modifying the BODIPY core to give structures that absorb at longer wavelengths. One of the most promising approaches to the modification of BOD-IPY is its peripheral functionalization with conjugated chromophores. Scheme 1.[a] Institute of Organic Chemistry, National Academy For example, distyryl-substituted derivatives A exhibit a bathochromic shift of the absorption maximum of 79 nm compared with diphenyl-substituted analogues (see Scheme 1). The bathochromic shift of phenylethynyl analogues B is somewhat smaller, however, both A and B are typical BODIPYs and demonstrate high fluorescence quantum yields that are fairly insensitive to the nature of the solvent.[3] The introduction of additional 4-(dialkylamino) substituents into A (structure C [4] ) results in even more pronounced spectral changes, with bathochromic shifts of around 80 nm. The structures C exhibit very small solvatochromism and considerable positive solvatofluorochromism. The fluorescence intensity increases significantly with decreasing solvent polarity. Protonation of the dialkylamino groups in C leads to optical properties that are very similar to those of A. Although the charge-separated mesomeric form C2 is typical of merocyanine dyes, the properties of the structures C (e.g., easy protonation, weak solvatochromism, and relatively low molar absorptivity) as a whole do not correspond to those of merocyanines. Thus, the dialkylamino groups in structures C provide considerable spectral changes, but do not change the color of the V. P. Yakubovskyi, M. P. Shandura, Y. P. Kovtun FULL PAPER BODIPY core. Therefore in this case they cannot be referred to as true "end groups" as defined in the ideology of polymethine dyes.This statement is even more evident for structures D. [3a,4b,5] In this case the dialkylamino group leads to a small hypsochromic shift of the BODIPY absorption maximum. The fluorescence quantum yields are quenched in polar solvents but not i...

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Series of polymethine dyes derived from 2,2-difluoro-1,3,2-(2H)-dioxaborine of 3-acetyl-7-diethylamino-4-hydroxycoumarin

Cited by 48 publications

References 18 publications

Polymethine dyes derived from the boron difluoride complex of 3-acetyl-5,7-di(pyrrolidin-1-yl)-4-hydroxycoumarin

Polymethine dyes derived from the boron difluoride complex of 3-acetyl-5,7-di(pyrrolidin-1-yl)-4-hydroxycoumarin

1,3,2‐(2H)‐dioxaborine polymethine dyes on the base of dehydroacetic acid — effective fluorescent amine probes

Boradipyrromethenecyanines

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