Convenient one-pot procedure for synthesizing 4,4′-dimethoxy-boradiaza-s-indacene dyes and their application to cell labeling

Liu, Kuan‐Miao; Tsai, Ming-Shiun; Jan, Ming‐Shiou; Chau, Chi-Min; Wang, Wan-Ju

doi:10.1016/j.tet.2011.08.043

Cited by 9 publications

(5 citation statements)

References 27 publications

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“…Although many BODIPYs functionalized at boron have been recently reported, including F-BODIPYs, ,− Cl-BODIPYs, − H-BODIPYs, C-BODIPYs, − O-BODIPYs, − OH-BODIPYs, , and CN-BODIPYs, − their stability and reactivity have not yet been comprehensively investigated. In 2011, Yan et al reported that a 4,4′-diphenyl-BODIPY was more stable under both acidic (using di or trichloroacetic acid) and basic conditions (using ammonium hydroxide) than the corresponding 4,4′-difluoro, 4,4′-dimethyl, and 4,4′-dimethoxy-BODIPYs, using 11 B NMR.…”

Section: Introductionmentioning

confidence: 99%

Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron

et al. 2018

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Boron-dipyrromethene (BODIPY) dyes have been extensively investigated in recent years for a variety of bioanalytical and bioimaging applications. The success of these applications relies on the stability of BODIPYs, particularly under acidic conditions. In this work, the stability of a series of 4,4′-disubstituted BODIPYs (−F, −CN, −Ph, −Me, −OMe) toward addition of excess trifluoroacetic acid (TFA) was studied systematically and comprehensively through 11B and 1H NMR, UV–vis, fluorescence, thin layer chromatography, mass spectrometry, and infrared. The results indicate that 4,4′-dicyano-BODIPY 2 is the most stable among this series and remains unchanged even 3 days after addition of excess TFA. On the other hand, 4,4′-dimethyl-BODIPY 3 and 4,4′-dimethoxy-BODIPY 5 are the least stable, toward addition of TFA, and the 4,4′-diphenyl and 4,4′-difluoro-BODIPYs 1 and 4 were found to have intermediate stability. The experimental analysis and comparison with theoretical calculations indicate that the 4,4′-dicyano-BODIPY 2 has the greater aromaticity of the series, as evaluated by the BLA parameter, decreased charge on boron, and upon TFA addition it forms an unusually stable BODIPY 2···TFA complex. On the other hand, all other BODIPYs decompose within hours after TFA addition. Computational modeling demonstrates that 4,4′-dicyano substitution increases aromaticity and stabilizes the B–N bond, resulting in the most stable compound from the series studied.

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Section: Introductionmentioning

confidence: 99%

Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron

et al. 2018

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“…[4][5][6] Recent research has focused on the synthesis of BODIPYs with substituents other than fluorine at the boron centre, with the goal of creating BODIPYs with unique spectroscopic properties. A wide range of B-alkynyl (E-BODIPY) and B-alkyl (C-BODIPY) derivatives have thus been synthesized, alongside other variants [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] including Cl-BODIPYs, compounds that allow for facile substitutions at the boron center courtesy of the weaker B-Cl bond cf. B-F bond.…”

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confidence: 99%

Activation and deprotection of F-BODIPYs using boron trihalides

2014

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“…[2,3] From the synthetic chemistry point of view, the skeleton of BODIPY has been further developed from the early symmetric structure to various asymmetric types of ligands anchoring on the À BF 2 moiety [4][5][6][7][8][9][10][11] or even À BR 2 groups, where the fluoride was replaced by other groups such as phenyl, À OCH 3 and others. [12][13][14][15][16] This asymmetric extension lies in several incentives. First, the emission Stokes shift, defined as the difference in frequency between the lowest lying absorption and emission maxima, is rather small for the symmetric boron compounds.…”

Section: Introductionmentioning

confidence: 99%

Substituent Effects in Six(Anilido)‐Five(Thiazole) Membered Ring Boron Difluoride Dyes

et al. 2021

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A series of new six (anilido)-five (thiazole) membered ring boron difluoride dyes, namely BFs, have been synthesized from the corresponding para-and meta-substituted 2-(2'-methylaminophenyl) benzothiazoles through complexation with boron trifluoride. Depending on the substituent effect, the derivatives can switch the emission properties from fluorescence with 100 % emission yield to slim fluorescence but > 90 % triplet state population and peak wavelength tuning from 490 nm to 610 nm. Compared with non-complexed precursors, the rigid, highly planar structure and significantly red-shifted absorption and emission for BFs indicate that the boron center facilitates the formation of a bridge leading to increased rigidity, and is also involved in π-conjugation, increasing the transition dipole and suppressing the nonradiative internal conversion. Together with optical ~100 % transparent window around 325-375 nm, BFs may find unique applications, among which the fluorescence up-conversion via triplet-triplet annihilation is demonstrated.

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Convenient one-pot procedure for synthesizing 4,4′-dimethoxy-boradiaza-s-indacene dyes and their application to cell labeling

Cited by 9 publications

References 27 publications

Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron

Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron

Activation and deprotection of F-BODIPYs using boron trihalides

Substituent Effects in Six(Anilido)‐Five(Thiazole) Membered Ring Boron Difluoride Dyes

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