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Synthesis, Photophysics, and Electrochemistry of Tetra(2‐thienyl)ethylene (TTE) Derivatives
Author(s) -
Bolzoni Alessandro,
Viglianti Lucia,
Bossi Alberto,
Mussini Patrizia R.,
Cauteruccio Silvia,
Baldoli Clara,
Licandro Emanuela
Publication year - 2013
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.201300745
Subject(s) - chemistry , tetra , electrophile , electrochemistry , ethylene , photochemistry , thiophene , homo/lumo , surface modification , organic chemistry , medicinal chemistry , molecule , electrode , catalysis
We have synthesized a series of tetra(2‐thienyl)ethylene (TTE) derivatives, selectively functionalized at the thiophene α positions, either by a coupling procedure or by direct electrophilic substitution of the TTE system. Optical spectroscopy revealed that TTE shows orange emission (470 nm) in a diluted 2‐MeTHF matrix at 77 K and blue (420 nm) aggregation‐induced emission (AIE) in the solid state. An exhaustive electrochemical study afforded a full rationalization of the electronic properties in terms of the HOMO and LUMO energy levels and gaps, as well as localization and features of the redox centers with respect to TTE functionalization.