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Pyrene–Azobenzene Dyads and Their Photochemistry
Author(s) -
Nachtigall Olaf,
Lomoth Reiner,
Dahlstrand Christian,
Lundstedt Anna,
Gogoll Adolf,
Webb Matthew J.,
Grennberg Helena
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301301
Subject(s) - azobenzene , chemistry , pyrene , photoisomerization , photochemistry , chromophore , isomerization , absorbance , fluorescence , quenching (fluorescence) , azo compound , molecule , organic chemistry , polymer , catalysis , physics , chromatography , quantum mechanics
The facile synthesis of three new folding azobenzene‐pyrene systems 1 – 3 , connected together by a serendipitously obtained and unpredicted ester linkage, is reported. Additional characterization of the photochemistry of these systems revealed variations in azobenzene photoisomerization ( trans‐cis and cis‐trans ) and quenching of pyrene fluorescence, as a result of intra‐excitation energy transfer from the pyrene chromophore to an azobenzene. Through the use of aryl substituent electronic effects to tune the absorption properties of the azobenzene relative to the pyrene, we show that efficient photo‐switching can be achieved when the trans ‐azobenzene absorbance band is well separated from that of the pyrene (compound 1 ), whereas overlap of the corresponding absorbance bands in the cases of 2 and 3 significantly compromises trans‐cis isomerization by enhancing cis‐trans interconversion.