Journal of Physical Chemistry A, volume 109, issue 33, pages 7371-7384
Photophysical Properties of Borondipyrromethene Analogues in Solution
Publication type: Journal Article
Publication date: 2005-08-01
Journal:
Journal of Physical Chemistry A
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.9
ISSN: 10895639, 15205215
Physical and Theoretical Chemistry
Abstract
The photophysical properties of seven new 8-(p-substituted)phenyl analogues of 4,4-difluoro-3,5-dimethyl-8-(aryl)-4-bora-3a,4a-diaza-s-indacene (derivatives of the well-known fluorophore BODIPY) in several solvents have been studied by means of absorption and steady-state and time-resolved fluorimetry. For each compound, the fluorescence quantum yield and lifetime are lower in solvents with higher polarity owing to an increase in the rate of nonradiative deactivation. Increasing the electron withdrawing strength of the p-substituent on the phenyl group in position 8 also leads to lower fluorescence quantum yields and lifetimes. When the p-substituent on the phenyl group in position 8 is a tertiary amine [8-(4-piperidinophenyl), 8-(4-N,N-dimethylaminophenyl), and 8-(4-morpholinophenyl)], the low quantum yields of these compounds in more polar solvents can be rationalized by the inversion of the energy levels of an apolar, highly fluorescent and a polar, nonfluorescent excited state, where charge transfer from the tertiary amine to the BODIPY unit occurs. These amine analogues can be protonated at low pH in aqueous solution. Fluorescence titrations yielded pK(a) values of their conjugate ammonium salts which are in agreement with the electron donating tendency of the amine group: piperidino (4.15) > dimethylamino (2.37) > morpholino (1.47), with the pK(a) values in parentheses. The rate constant of radiative deactivation (k(f)) is the same for all compounds in all solvents studied (k(f) = 1.4 x 10(8) s(-1)).
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Qin W. et al. Photophysical Properties of Borondipyrromethene Analogues in Solution // Journal of Physical Chemistry A. 2005. Vol. 109. No. 33. pp. 7371-7384.
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Qin W., Baruah M., Auweraer M. V. D., De Schryver F. C., Boens N. Photophysical Properties of Borondipyrromethene Analogues in Solution // Journal of Physical Chemistry A. 2005. Vol. 109. No. 33. pp. 7371-7384.
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TY - JOUR
DO - 10.1021/jp052626n
UR - https://doi.org/10.1021%2Fjp052626n
TI - Photophysical Properties of Borondipyrromethene Analogues in Solution
T2 - Journal of Physical Chemistry A
AU - Qin, Wenwu
AU - Baruah, Mukulesh
AU - De Schryver, Frans C.
AU - Boens, Noël
AU - Auweraer, Mark Van der
PY - 2005
DA - 2005/08/01 00:00:00
PB - American Chemical Society (ACS)
SP - 7371-7384
IS - 33
VL - 109
SN - 1089-5639
SN - 1520-5215
ER -
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@article{2005_Qin
author = {Wenwu Qin and Mukulesh Baruah and Frans C. De Schryver and Noël Boens and Mark Van der Auweraer},
title = {Photophysical Properties of Borondipyrromethene Analogues in Solution},
journal = {Journal of Physical Chemistry A},
year = {2005},
volume = {109},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021%2Fjp052626n},
number = {33},
pages = {7371--7384},
doi = {10.1021/jp052626n}
}
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MLA
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Qin, Wenwu, et al. “Photophysical Properties of Borondipyrromethene Analogues in Solution.” Journal of Physical Chemistry A, vol. 109, no. 33, Aug. 2005, pp. 7371-7384. https://doi.org/10.1021%2Fjp052626n.