Synthesis and photochromic behaviour of a series of benzopyrans bearing an N-phenyl-carbazole moiety: photochromism control by the steric effect

Author:

Frigoli Michel12345ORCID,Jousselin-Oba Tanguy12345,Mamada Masashi67899ORCID,Marrot Jérôme12345,Zangarelli Agnese1011121314,Pannacci Danilo1011121314,Adachi Chihaya67899ORCID,Ortica Fausto1011121314ORCID

Affiliation:

1. Université Paris-Saclay

2. UVSQ

3. UMR CNRS 8080

4. Institut Lavoisier de Versailles

5. 78035 Versailles

6. Center for Organic Photonics and Electronics Research (OPERA)

7. JST ERATO Adachi Molecular Exciton Engineering Project

8. and Academia-Industry Molecular Systems for Devices Research and Education Center

9. Kyushu University

10. Dipartimento di Chimica

11. Biologia e Biotecnologie

12. Università degli Studi di Perugia

13. 06123 Perugia

14. Italy

Abstract

The phenyl group in blue controls the photochromism of [3H]-naphthopyran derivatives by favouring the photoinduced formation of the TT isomer over TC at the photostationary state by steric hindrance.

Funder

Università degli Studi di Perugia

Istituto Nazionale di Fisica Nucleare

Japan Society for the Promotion of Science

Agence Nationale de la Recherche

Centre National de la Recherche Scientifique

Japan Science and Technology Agency

Publisher

Springer Science and Business Media LLC

Subject

Physical and Theoretical Chemistry

Reference42 articles.

1. B. Van Gemert , in Organic Photochromic and Thermochromic Compounds , ed. J. C. Crano and R. J. Guglielmetti , Kluwer Academic/Plenum Publishers , New York , 1999 , vol. 1 , pp. 111–140

2. J. D. Hepworth and B. M.Heron , in Functional Dyes , ed. S.-H. Kim , Amsterdam , Elsevier , 2006 , pp. 85–135

3. Industrial organic photochromic dyes

4. Proof of structure of the colored photoproducts of chromenes and spiropyrans

5. Photophysics, photochemistry and kinetics of photochromic 2H-pyrans and chromenes

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