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Synthesis and Physical Chemistry of s ‐Tetrazines: Which Ones are Fluorescent and Why?
Author(s) -
Gong YongHua,
Miomandre Fabien,
MéalletRenault Rachel,
Badré Sophie,
Galmiche Laurent,
Tang Jie,
Audebert Pierre,
Clavier Gilles
Publication year - 2009
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.200900964
Subject(s) - chemistry , heteroatom , fluorescence , electrochemistry , photochemistry , nanotechnology , organic chemistry , physics , materials science , quantum mechanics , ring (chemistry) , electrode
New fluorescent tetrazines have been prepared and their electrochemistry and fluorescence efficiency evaluated. The occurrence of fluorescence as well as the wavelength were found to be strongly dependent on the substituents, which have to be electronegative heteroatoms. This has been rationalized through a computational study that showed that the crucial factor is the nature of the HOMO, which determines the existence or not of fluorescence. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)