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Continuous Symmetry Breaking Induced by Ion Pairing Effect in Heptamethine Cyanine Dyes: Beyond the Cyanine Limit
Abstract
The association of heptamethine cyanine cation 1(+) with various counterions A (A = Br(-), I(-), PF(6)(-), SbF(6)(-), B(C(6)F(5))(4)(-), TRISPHAT) was realized. The six different ion pairs have been characterized by X-ray diffraction, and their absorption properties were studied in polar (DCM) and apolar (toluene) solvents. A small, hard anion (Br(-)) is able to strongly polarize the polymethine chain, resulting in the stabilization of an asymmetric dipolar-like structure in the crystal and in nondissociating solvents. On the contrary, in more polar solvents or when it is associated with a bulky soft anion (TRISPHAT or B(C(6)F(5))(4)(-)), the same cyanine dye adopts preferentially the ideal polymethine state. The solid-state and solution absorption properties of heptamethine dyes are therefore strongly correlated to the nature of the counterion.
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Cited by
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Li, Y., Cai, Z., Liu, S., Zhang, H., Wong, S. T. H., Lam, J. W. Y., Kwok, R. T. K., Qian, J., & Tang, B. Z. (2020) · Nature Communications · doi:10.1038/s41467-020-15095-1 · Cited by 464
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Metadata
- Authors
- Bouit, P.-A., Aronica, C., Toupet, L., Le Guennic, B., Andraud, C., & Maury, O.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-03-04
- Volume
- 132
- Issue
- 12
- Pages
- 4328-4335
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2053238537
- Cited by
- 207
- References
- 0
- FWCI
- 4.67
- Type
- journal article
- Language
- en
- Open access
- closed
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- Bouit, P.-A., Aronica, C., Toupet, L., Le Guennic, B., Andraud, C., & Maury, O. (2010). Continuous Symmetry Breaking Induced by Ion Pairing Effect in Heptamethine Cyanine Dyes: Beyond the Cyanine Limit. Journal of the American Chemical Society. https://doi.org/10.1021/ja9100886
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