A multifunctional photoswitch: 6π electrocyclization versus esipt and metalation

Juliette Guérin; Anne Léaustic; Stéphanie Delbaere; Jérôme Berthet; Régis Guillot; Cyril Ruckebusch; Rémi Métivier; Keitaro Nakatani; Maylis Orio; Michel Sliwa; Pei Yu

doi:10.1002/chem.201402448

A multifunctional photoswitch: 6π electrocyclization versus esipt and metalation

Juliette Guérin
, Anne Léaustic
, Stéphanie Delbaere
, Jérôme Berthet
, Régis Guillot
, Cyril Ruckebusch
, Rémi Métivier
, Keitaro Nakatani
, Maylis Orio
, Michel Sliwa
, Pei Yu

Institut de Chimie Moléculaire et des Matériaux d'Orsay
Université de Lille
Laboratoire de Spectrochimie Infrarouge et Raman, Université des Sciences et Technologies de Lille, UMR-CNRS 8516
ENS Paris-Saclay

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

Abstract

A terthiazole-based molecular switch associating 6π electrocyclization, excited state intramolecular proton transfer (ESIPT), and strong metal binding capability was prepared. The photochemical and photophysical properties of this molecule and of the corresponding nickel and copper complexes were thoroughly investigated by steady-state and ultrafast absorption spectroscopy and rationalized by DFT/TDDFT calculations. The switch behaves as a biphotochrome with time-dependent photochemical outcome and displays efficient ESIPT-based fluorescence photoswitching. Both photochemical reactions are suppressed by nickel or copper metalation, and the main factors contributing to the quenching of the electrocyclization are discussed.

Original language	English
Pages (from-to)	12279-12288
Number of pages	10
Journal	Chemistry - A European Journal
Volume	20
Issue number	38
DOIs	https://doi.org/10.1002/chem.201402448
Publication status	Published - 15 Sept 2014
Externally published	Yes

Keywords

density functional calculations
femtosecond chemistry
intramolecular proton transfer
metalation
photochromism

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10.1002/chem.201402448

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title = "A multifunctional photoswitch: 6π electrocyclization versus esipt and metalation",

abstract = "A terthiazole-based molecular switch associating 6π electrocyclization, excited state intramolecular proton transfer (ESIPT), and strong metal binding capability was prepared. The photochemical and photophysical properties of this molecule and of the corresponding nickel and copper complexes were thoroughly investigated by steady-state and ultrafast absorption spectroscopy and rationalized by DFT/TDDFT calculations. The switch behaves as a biphotochrome with time-dependent photochemical outcome and displays efficient ESIPT-based fluorescence photoswitching. Both photochemical reactions are suppressed by nickel or copper metalation, and the main factors contributing to the quenching of the electrocyclization are discussed.",

keywords = "density functional calculations, femtosecond chemistry, intramolecular proton transfer, metalation, photochromism",

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year = "2014",

month = sep,

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doi = "10.1002/chem.201402448",

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TY - JOUR

T1 - A multifunctional photoswitch

T2 - 6π electrocyclization versus esipt and metalation

AU - Guérin, Juliette

AU - Léaustic, Anne

AU - Delbaere, Stéphanie

AU - Berthet, Jérôme

AU - Guillot, Régis

AU - Ruckebusch, Cyril

AU - Métivier, Rémi

AU - Nakatani, Keitaro

AU - Orio, Maylis

AU - Sliwa, Michel

AU - Yu, Pei

PY - 2014/9/15

Y1 - 2014/9/15

N2 - A terthiazole-based molecular switch associating 6π electrocyclization, excited state intramolecular proton transfer (ESIPT), and strong metal binding capability was prepared. The photochemical and photophysical properties of this molecule and of the corresponding nickel and copper complexes were thoroughly investigated by steady-state and ultrafast absorption spectroscopy and rationalized by DFT/TDDFT calculations. The switch behaves as a biphotochrome with time-dependent photochemical outcome and displays efficient ESIPT-based fluorescence photoswitching. Both photochemical reactions are suppressed by nickel or copper metalation, and the main factors contributing to the quenching of the electrocyclization are discussed.

AB - A terthiazole-based molecular switch associating 6π electrocyclization, excited state intramolecular proton transfer (ESIPT), and strong metal binding capability was prepared. The photochemical and photophysical properties of this molecule and of the corresponding nickel and copper complexes were thoroughly investigated by steady-state and ultrafast absorption spectroscopy and rationalized by DFT/TDDFT calculations. The switch behaves as a biphotochrome with time-dependent photochemical outcome and displays efficient ESIPT-based fluorescence photoswitching. Both photochemical reactions are suppressed by nickel or copper metalation, and the main factors contributing to the quenching of the electrocyclization are discussed.

KW - density functional calculations

KW - femtosecond chemistry

KW - intramolecular proton transfer

KW - metalation

KW - photochromism

UR - https://www.scopus.com/pages/publications/84925446181

U2 - 10.1002/chem.201402448

DO - 10.1002/chem.201402448

M3 - Article

AN - SCOPUS:84925446181

SN - 0947-6539

VL - 20

SP - 12279

EP - 12288

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 38

ER -

A multifunctional photoswitch: 6π electrocyclization versus esipt and metalation

Abstract

Keywords

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