TY - JOUR
T1 - Synthesis and properties of molecular switches based on the opening and closing of oxazine rings
AU - Deniz, Erhan
AU - Cusido, Janet
AU - Swaminathan, Subramani
AU - Battal, Mutlu
AU - Impellizzeri, Stefania
AU - Sortino, Salvatore
AU - Raymo, Françisco M.
N1 - Funding Information:
FMR thanks the National Science Foundation (CAREER Award CHE-0237578, CHE-0749840 and CHE-1049860) for supporting his research program and for providing funds to purchase a mass spectrometer (CHE-0946858). SS thanks the MIUR (PRIN 2008) for financial support and the Royal Society of Chemistry for a travel grant.
PY - 2012/2/1
Y1 - 2012/2/1
N2 - We designed and synthesized a family of molecular switches each pairing an oxazine ring to a chromophoric fragment. Under the influence of either chemical or optical stimulations, the oxazine ring opens to bring the chromophoric appendage in conjugation with either a 3H-indolium cation or a phenolate anion. These structural transformations alter the electronic structure of the chromophore and, as a result, its electrochemical and spectroscopic signatures. Specifically, we demonstrated that the absorption of triphenylamine and thiophene fragments, the fluorescence of a coumarin appendage and the oxidation potential of a ferrocene center can all be switched with acid, base or ultraviolet inputs. Thus, these operating principles and structural designs for switching properties at the molecular level with the aid of external stimulations might eventually lead to a general strategy for the realization of chemo- and photo-responsive materials.
AB - We designed and synthesized a family of molecular switches each pairing an oxazine ring to a chromophoric fragment. Under the influence of either chemical or optical stimulations, the oxazine ring opens to bring the chromophoric appendage in conjugation with either a 3H-indolium cation or a phenolate anion. These structural transformations alter the electronic structure of the chromophore and, as a result, its electrochemical and spectroscopic signatures. Specifically, we demonstrated that the absorption of triphenylamine and thiophene fragments, the fluorescence of a coumarin appendage and the oxidation potential of a ferrocene center can all be switched with acid, base or ultraviolet inputs. Thus, these operating principles and structural designs for switching properties at the molecular level with the aid of external stimulations might eventually lead to a general strategy for the realization of chemo- and photo-responsive materials.
KW - Fluorescence
KW - Halochromism
KW - Molecular switches
KW - Oxazines
KW - Photochromism
UR - http://www.scopus.com/inward/record.url?scp=84855593250&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84855593250&partnerID=8YFLogxK
U2 - 10.1016/j.jphotochem.2011.11.008
DO - 10.1016/j.jphotochem.2011.11.008
M3 - Article
AN - SCOPUS:84855593250
VL - 229
SP - 20
EP - 28
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
IS - 1
ER -