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Structural Control of the Photodynamics of Boron−Dipyrrin Complexes
Open accessAbstract
Boron-dipyrrin chromophores containing a 5-aryl group with or without internal steric hindrance toward aryl rotation have been synthesized and then characterized via X-ray diffraction, static and time-resolved optical spectroscopy, and theory. Compounds with a 5-phenyl or 5-(4-tert-butylphenyl) group show low fluorescence yields (approximately 0.06) and short excited-singlet-state lifetimes (approximately 500 ps), and decay primarily (>90%) by nonradiative internal conversion to the ground state. In contrast, sterically hindered analogues having an o-tolyl or mesityl group at the 5-position exhibit high fluorescence yields (approximately 0.9) and long excited-state lifetimes (approximately 6 ns). The X-ray structures indicate that the phenyl or 4-tert-butylphenyl ring lies at an angle of approximately 60 degrees with respect to the dipyrrin framework whereas the angle is approximately 80 degrees for mesityl or o-tolyl groups. The calculated potential energy surface for the phenyl-substituted complex indicates that the excited state has a second, lower energy minimum in which the nonhindered aryl ring rotates closer to the mean plane of the dipyrrin, which itself undergoes some distortion. This relaxed, distorted excited-state conformation has low radiative probability as well as a reduced energy gap from the ground state supporting a favorable vibrational overlap factor for nonradiative deactivation. Such a distorted conformation is energetically inaccessible in a complex bearing the sterically hindered o-tolyl or mesityl group at the 5-position, leading to a high radiative probability involving conformations at or near the initial Franck-Condon form of the excited state. These combined results demonstrate the critical role of aryl-ring rotation in governing the excited-state dynamics of this class of widely used dyes.
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Metadata
- Authors
- Kee, H. L., Kirmaier, C., Yu, L., Thamyongkit, P., Youngblood, W. J., Calder, M. E., Ramos, L., Noll, B. C., Bocian, D. F., Scheidt, W. R., Birge, R. R., Lindsey, J. S., & Holten, D.
- Venue
- The Journal of Physical Chemistry B
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-10-08
- Volume
- 109
- Issue
- 43
- Pages
- 20433-20443
- ISSN
- 1520-5207 (ISSN-L)
- 1520-6106
- OpenAlex
- W2144149256
- Cited by
- 425
- References
- 19
- FWCI
- 4.84
- Type
- journal article
- Language
- en
- Open access
- green
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