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Continuous Symmetry Breaking Induced by Ion Pairing Effect in Heptamethine Cyanine Dyes: Beyond the Cyanine Limit

Bouit, Pierre-Antoine, Aronica, Christophe, Toupet, Loïc, Le Guennic, Boris, Andraud, Chantal, Maury, Olivier·2010·Journal of the American Chemical Society

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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Metadata

Authors
Bouit, P.-A., Aronica, C., Toupet, L., Le Guennic, B., Andraud, C., & Maury, O.
Venue
Journal of the American Chemical Society
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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CoChat. (2026). Citation check: Continuous Symmetry Breaking Induced by Ion Pairing Effect in Heptamethine Cyanine Dyes: Beyond the Cyanine Limit. https://app.cochat.ai/papers/10.1021/ja9100886
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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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