Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly

Leonard J. Prins; Christoph Thalacker; Frank Würthner; Peter Timmerman; David N. Reinhoudt

doi:10.1073/pnas.171131398

Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly

Leonard J. Prins, Christoph Thalacker, Frank Würthner, Peter Timmerman, David N. Reinhoudt

Faculty of Science and Technology

Research output: Contribution to journal › Article › Academic › peer-review

52 Citations (Scopus)

59 Downloads (Pure)

Abstract

Multichromophoric hydrogen-bonded assemblies 13⋅(BAR)6 are studied that bear a remarkably close resemblance to commelinin, a naturally occurring assembly responsible for an intense blue color of flowers. The incorporated chromophores exhibit a hypsochromic shift in the UV/visible (Vis) absorption maximum (Δ λmax = 14 nm) compared with the free chromophores. In addition, the chiroptical properties of incorporated chromophores can be rationally controlled by changing the supramolecular chirality of the assembly. These properties have been used to study the stability of this type of assembly with UV and CD spectroscopy at concentrations far below the NMR sensitivity threshold (10−4 M). The determined C50% values of 2–3 μM in benzene show the extremely high stability of these hydrogen-bonded assemblies.

Original language	English
Pages (from-to)	10042-10045
Journal	Proceedings of the National Academy of Sciences of the United States of America
Volume	98
Issue number	18
DOIs	https://doi.org/10.1073/pnas.171131398
Publication status	Published - 2001

Keywords

IR-36756
METIS-202978

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Prins2001chiral
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title = "Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly",

abstract = "Multichromophoric hydrogen-bonded assemblies 13⋅(BAR)6 are studied that bear a remarkably close resemblance to commelinin, a naturally occurring assembly responsible for an intense blue color of flowers. The incorporated chromophores exhibit a hypsochromic shift in the UV/visible (Vis) absorption maximum (Δ λmax = 14 nm) compared with the free chromophores. In addition, the chiroptical properties of incorporated chromophores can be rationally controlled by changing the supramolecular chirality of the assembly. These properties have been used to study the stability of this type of assembly with UV and CD spectroscopy at concentrations far below the NMR sensitivity threshold (10−4 M). The determined C50% values of 2–3 μM in benzene show the extremely high stability of these hydrogen-bonded assemblies.",

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Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly. / Prins, Leonard J.; Thalacker, Christoph; Würthner, Frank; Timmerman, Peter; Reinhoudt, David N.

In: Proceedings of the National Academy of Sciences of the United States of America, Vol. 98, No. 18, 2001, p. 10042-10045.

Research output: Contribution to journal › Article › Academic › peer-review

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T1 - Chiral exciton coupling of merocyanine dyes within a well defined hydrogen-bonded assembly

AU - Prins, Leonard J.

AU - Thalacker, Christoph

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AU - Reinhoudt, David N.

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N2 - Multichromophoric hydrogen-bonded assemblies 13⋅(BAR)6 are studied that bear a remarkably close resemblance to commelinin, a naturally occurring assembly responsible for an intense blue color of flowers. The incorporated chromophores exhibit a hypsochromic shift in the UV/visible (Vis) absorption maximum (Δ λmax = 14 nm) compared with the free chromophores. In addition, the chiroptical properties of incorporated chromophores can be rationally controlled by changing the supramolecular chirality of the assembly. These properties have been used to study the stability of this type of assembly with UV and CD spectroscopy at concentrations far below the NMR sensitivity threshold (10−4 M). The determined C50% values of 2–3 μM in benzene show the extremely high stability of these hydrogen-bonded assemblies.

AB - Multichromophoric hydrogen-bonded assemblies 13⋅(BAR)6 are studied that bear a remarkably close resemblance to commelinin, a naturally occurring assembly responsible for an intense blue color of flowers. The incorporated chromophores exhibit a hypsochromic shift in the UV/visible (Vis) absorption maximum (Δ λmax = 14 nm) compared with the free chromophores. In addition, the chiroptical properties of incorporated chromophores can be rationally controlled by changing the supramolecular chirality of the assembly. These properties have been used to study the stability of this type of assembly with UV and CD spectroscopy at concentrations far below the NMR sensitivity threshold (10−4 M). The determined C50% values of 2–3 μM in benzene show the extremely high stability of these hydrogen-bonded assemblies.

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JO - Proceedings of the National Academy of Sciences of the United States of America

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