Tuning the Activation Wavelength of Photochromic Oxazines

Subramani Swaminathan; Jaume Garcia-Amorós; Ek Raj Thapaliya; Santi Nonell; Burjor Captain; Françisco M Raymo

doi:10.1002/cphc.201600141

Tuning the Activation Wavelength of Photochromic Oxazines

Chemphyschem. 2016 Jun 17;17(12):1852-9. doi: 10.1002/cphc.201600141. Epub 2016 Mar 31.

Authors

Subramani Swaminathan¹, Jaume Garcia-Amorós^{1

2}, Ek Raj Thapaliya¹, Santi Nonell³, Burjor Captain¹, Françisco M Raymo⁴

Affiliations

¹ Laboratory for Molecular Photonics, Department of Chemistry, University of Miami, 1301 Memorial Drive, Florida, 33146-0431, USA.
² Grup de Materials Orgànics, Institut de Nanociència i Nanotecnologia (IN2UB), Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1, E-08028, Barcelona, Spain.
³ Grup O'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramón Llull, Via Augusta 390, E-08017, Barcelona, Spain.
⁴ Laboratory for Molecular Photonics, Department of Chemistry, University of Miami, 1301 Memorial Drive, Florida, 33146-0431, USA. [email protected].

PMID: 27003328
DOI: 10.1002/cphc.201600141

Abstract

The activation wavelength of a photochromic oxazine can be shifted bathochromically with the introduction of a methoxy substituent on the chromophore responsible for initiating the photochemical transformation. This structural modification permits switching under mild illumination conditions, enhances the photoisomerization quantum yield and ensures outstanding fatigue resistance. Thus, these results can guide the design of new members of this family of photoresponsive molecular switches with improved photochemical and photophysical properties.

Keywords: heterocycles; isomerization; molecular switches; oxazines; photochromism.