Chiroptical switching based on photoinduced proton transfer between homopolymers bearing side-chain spiropyran and azopyridine moieties

Luigi Angiolini; Tiziana Benelli; Loris Giorgini; Françisco M. Raymo

doi:10.1002/macp.200800192

Chiroptical switching based on photoinduced proton transfer between homopolymers bearing side-chain spiropyran and azopyridine moieties

Luigi Angiolini, Tiziana Benelli, Loris Giorgini, Françisco M. Raymo

Chemistry

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

22 Scopus citations

Abstract

A novel optically-active polymeric methacrylate, bearing the (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, was synthesized and investigated in combination with a polymeric methacrylate incorporating the photoisomerizable spiropyran chromophore in the sidechain. In the presence of acid, this system can be operated in solution to modulate the protonation of the azopyridine moieties by photoisomerizing the spiropyran component. In addition to UV-vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, thus behaving as a chiroptical switch.

Original language	English (US)
Pages (from-to)	2049-2060
Number of pages	12
Journal	Macromolecular Chemistry and Physics
Volume	209
Issue number	19
DOIs	https://doi.org/10.1002/macp.200800192
State	Published - Oct 7 2008

Keywords

Amplification of chirality
Chiroptical switches
Photochromism
Polymeric azopyridine
Polymeric spiropyran

ASJC Scopus subject areas

Materials Chemistry
Polymers and Plastics
Organic Chemistry
Physical and Theoretical Chemistry
Condensed Matter Physics

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10.1002/macp.200800192

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title = "Chiroptical switching based on photoinduced proton transfer between homopolymers bearing side-chain spiropyran and azopyridine moieties",

abstract = "A novel optically-active polymeric methacrylate, bearing the (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, was synthesized and investigated in combination with a polymeric methacrylate incorporating the photoisomerizable spiropyran chromophore in the sidechain. In the presence of acid, this system can be operated in solution to modulate the protonation of the azopyridine moieties by photoisomerizing the spiropyran component. In addition to UV-vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, thus behaving as a chiroptical switch.",

keywords = "Amplification of chirality, Chiroptical switches, Photochromism, Polymeric azopyridine, Polymeric spiropyran",

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AU - Angiolini, Luigi

AU - Benelli, Tiziana

AU - Giorgini, Loris

AU - Raymo, Françisco M.

PY - 2008/10/7

Y1 - 2008/10/7

N2 - A novel optically-active polymeric methacrylate, bearing the (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, was synthesized and investigated in combination with a polymeric methacrylate incorporating the photoisomerizable spiropyran chromophore in the sidechain. In the presence of acid, this system can be operated in solution to modulate the protonation of the azopyridine moieties by photoisomerizing the spiropyran component. In addition to UV-vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, thus behaving as a chiroptical switch.

AB - A novel optically-active polymeric methacrylate, bearing the (S)-3-hydroxy pyrrolidinyl group linked through the nitrogen atom to an azopyridine chromophore, was synthesized and investigated in combination with a polymeric methacrylate incorporating the photoisomerizable spiropyran chromophore in the sidechain. In the presence of acid, this system can be operated in solution to modulate the protonation of the azopyridine moieties by photoisomerizing the spiropyran component. In addition to UV-vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, thus behaving as a chiroptical switch.

KW - Amplification of chirality

KW - Chiroptical switches

KW - Photochromism

KW - Polymeric azopyridine

KW - Polymeric spiropyran

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Chiroptical switching based on photoinduced proton transfer between homopolymers bearing side-chain spiropyran and azopyridine moieties

Abstract

Keywords

ASJC Scopus subject areas

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