Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles

Schwedler S, Eickhoff D, Brockhinke R, Cherian D, Weber L, Brockhinke A (2011)
Physical Chemistry Chemical Physics 13(20): 9301-9310.

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Abstract
Static and time-resolved fluorescence studies were carried out to investigate the photophysical properties and fluoride sensing abilities of highly fluorescent thienyl-containing 1,3-diethyl-1,3,2-benzodiazaboroles. Absorption and fluorescence spectra were measured in various solvents, showing the fluorophores to emit in the visible wavelength region with colors varying from blue to orange and quantum yields ranging between 0.21 and 1. Measured Stokes shifts of 2898 cm(-1) to 9308 cm(-1) were used to calculate the difference between excited-and ground-state dipole moments of the fluorophores. Values up to 18.8 D are of the same magnitude as for designed polarity probes such as PRODAN, supporting the idea of internal charge transfer transitions. Quenching studies with pyridine observing static and time-resolved fluorescence revealed a purely dynamic quenching mechanism and low Lewis acidity of the boron within the benzodiazaborolyl moiety compared to other triarylboranes. In contrast to this, quenching with fluoride was shown to stem from adduct formation. Reversible complexation of fluoride follows a simple mechanism for multi-functionalized benzodiazaboroles 2b and 2c, while those containing only one benzodiazaborole moiety (1 and 2a) show a more complicated behaviour, which might be explained by aggregation. Combining a benzodiazaborole group and a dimesitylborane function results in spectrally switchable fluoride sensors 3a and 3b, since the two boron sides can be deactivated for fluorescence in a stepwise manner.
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Schwedler S, Eickhoff D, Brockhinke R, Cherian D, Weber L, Brockhinke A. Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles. Physical Chemistry Chemical Physics. 2011;13(20):9301-9310.
Schwedler, S., Eickhoff, D., Brockhinke, R., Cherian, D., Weber, L., & Brockhinke, A. (2011). Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles. Physical Chemistry Chemical Physics, 13(20), 9301-9310.
Schwedler, S., Eickhoff, D., Brockhinke, R., Cherian, D., Weber, L., and Brockhinke, A. (2011). Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles. Physical Chemistry Chemical Physics 13, 9301-9310.
Schwedler, S., et al., 2011. Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles. Physical Chemistry Chemical Physics, 13(20), p 9301-9310.
S. Schwedler, et al., “Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles”, Physical Chemistry Chemical Physics, vol. 13, 2011, pp. 9301-9310.
Schwedler, S., Eickhoff, D., Brockhinke, R., Cherian, D., Weber, L., Brockhinke, A.: Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles. Physical Chemistry Chemical Physics. 13, 9301-9310 (2011).
Schwedler, Stefanie, Eickhoff, Daniel, Brockhinke, Regina, Cherian, Deepa, Weber, Lothar, and Brockhinke, Andreas. “Solvatochromism and fluoride sensing of thienyl-containing benzodiazaboroles”. Physical Chemistry Chemical Physics 13.20 (2011): 9301-9310.
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8 Citations in Europe PMC

Data provided by Europe PubMed Central.

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On the ambiguity of 1,3,2-benzodiazaboroles as donor/acceptor functionalities in luminescent molecules.
Weber L, Halama J, Hanke K, Bohling L, Brockhinke A, Stammler HG, Neumann B, Fox MA., Dalton Trans 43(8), 2014
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C,C'-bis(benzodiazaborolyl)dicarba-closo-dodecaboranes: synthesis, structures, photophysics and electrochemistry.
Weber L, Kahlert J, Brockhinke R, Bohling L, Halama J, Brockhinke A, Stammler HG, Neumann B, Nervi C, Harder RA, Fox MA., Dalton Trans 42(30), 2013
PMID: 23793134
Electrochemical and spectroelectrochemical studies of C-benzodiazaborolyl-ortho-carboranes.
Weber L, Kahlert J, Bohling L, Brockhinke A, Stammler HG, Neumann B, Harder RA, Low PJ, Fox MA., Dalton Trans 42(6), 2013
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Diazaborolyl-boryl push-pull systems with ethynylene-arylene bridges as 'turn-on' fluoride sensors.
Weber L, Eickhoff D, Kahlert J, Bohling L, Brockhinke A, Stammler HG, Neumann B, Fox MA., Dalton Trans 41(34), 2012
PMID: 22810804
Syntheses of rod-shaped fluorescent 1,3,2-benzodiazaboroles with phosphonium, and phosphane chalcogenide acceptor functions.
Weber L, Kuhtz H, Bohling L, Brockhinke A, Chrostowska A, Dargelos A, Maziere A, Stammler HG, Neumann B., Dalton Trans 41(34), 2012
PMID: 22797550
Luminescence properties of C-diazaborolyl-ortho-carboranes as donor-acceptor systems.
Weber L, Kahlert J, Brockhinke R, Bohling L, Brockhinke A, Stammler HG, Neumann B, Harder RA, Fox MA., Chemistry 18(27), 2012
PMID: 22623079
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Weber L, Eickhoff D, Marder TB, Fox MA, Low PJ, Dwyer AD, Tozer DJ, Schwedler S, Brockhinke A, Stammler HG, Neumann B., Chemistry 18(5), 2012
PMID: 22213064

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