Computational Design, Synthesis, and Mechanochromic Properties of New Thiophene-Based π-Conjugated Chromophores

Project name: 
POLOPTEL
TitleComputational Design, Synthesis, and Mechanochromic Properties of New Thiophene-Based π-Conjugated Chromophores
Publication TypeJournal Article
Year of Publication2013
AuthorsPrampolini, G, Bellina, F, Biczysko, M, Cappelli, C, Carta, L, Lessi, M, Pucci, A, Ruggeri, G, Barone, V
JournalChemistry-A European Journal
Volume19
Pagination1996 – 2004
Abstract

The possibility of exploiting supramolecular architectures for the preparation of innovative mechano- chromic devices has been extended by designing novel thienyl-substituted 1,4-bis-(ethynyl)benzene dyes, which are characterized by a conjugated, rigid, rodlike core structure. This new family of chromophores was synthesized according to a simple two-step sequential cross-coupling reaction, and the optical properties were investigated in solution and in a polymeric matrix. To tune the mechanochromic performances in smart polymer materials, a virtualscreening was set up that was able to select a derivative with optimal spectral features. The effective combination of experimental and computational investigations allowed us to spot those ho- mologues with already potential aniso- tropic and aggregachromic features and characterized by the best spectral properties and luminescent response. The best candidate was synthesized and dis- persed into a polyethylene matrix, indeed achieving an “in silico designed” mechanochromic material. Besides the specific applications of this novel material, the integration of com- putational and experimental techniques reported here defines an efficient protocol that can be applied to make a se- lection among similar dye candidates, which constitute the essential responsive part of such supramolecular devices.

DOI10.1002/chem.201203672