Synthesis, Photophysics, and Electrochemistry of Tetra(2‐thienyl)ethylene (TTE) Derivatives. Issue 33 (28th August 2013)

• Record Type: Journal Article
• Authors: Bolzoni, Alessandro; Viglianti, Lucia; Bossi, Alberto; Mussini, Patrizia R.; Cauteruccio, Silvia; Baldoli, Clara; Licandro, Emanuela
• Is Part Of: European journal of organic chemistry. Issue 33(2013)
• Page Start: 7489
• Page End: 7499
• Publication Date: 2013-08-28
• Subjects: Cross‐coupling -- Fluorescence -- Electrochemistry -- Sulfur heterocycles -- Solid‐state emission; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300745
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : A series of new TTE derivatives, selectively functionalized at the thiophene α positions, have been synthesized and structurally characterized. The electronic properties of TTE and its derivatives were elucidated by electrochemistry and optical spectroscopy revealed that TTE shows orange emission in a diluted 2‐MeTHF matrix at 77 K and blue aggregation‐induced emission in the solid state.