Synthesis, Electrochemistry, Crystal Structures, and Optical Properties of Quinoline Derivatives with a 2,2′‐Bithiophene Motif

Abstract

New quinolines bearing a 2,2Ј-bithiophene motif have been prepared through Ru-and In-catalyzed reactions as well as by Suzuki cross-coupling reactions. The novel quinolines have been characterized by using EI-HRMS and NMR spectroscopy. Additionally, the molecular structures of the novel quinolines were confirmed by X-ray crystallography. The photophysical and electrochemical properties of all quinoline derivatives were investigated by using absorption and luminescence spectroscopy and cyclic voltammetry. The main intense absorption bands associated with the quinoline derivatives were located between 350 and 450 nm. Intense blue-

Synthesis and photophysical properties of novel multisubstituted benzene and naphthalene derivatives with high 2D-π-conjugation

“…Surprisingly, in the case of M7, M6, M8 dimerization through bitiophenyl units does not occur -in this situation growing of the p-p ⁄ quaterthiophene absorption band at a slightly lower energy (100 nm, approximately) would arise, as we reported previously [55].…”

Small Donor–Acceptor Molecules Based on a Quinoline–Fluorene System with Promising Photovoltaic Properties

“…Our synthetic strategy began with the preparation of 2‐ethynyl‐9 H ‐fluorene ( 2 ) in a four‐step synthesis according to the literature methods or their minor modification 44,45. The 2‐fluorenyl‐substituted quinoline derivatives 4a – 4d were synthesized by our previously reported method 43. The reactions between commercially available acylanilines 3a – 3d and 2‐ethynyl‐9 H ‐fluorene ( 2 ) in the presence of the [Ru 3 (CO) 12 ]/HBF 4 catalytic system were key to the formation of the quinoline derivatives 4a – 4d .…”

“…We recently presented quinoline derivatives bearing a bithiophene motif that exhibited high luminescence depending on the substituents of the quinoline ring 43. Inspired by the potential of fluorene in optoelectronics, we exchanged the bithiophene motif for a fluoren‐2‐yl group in the quinoline scaffold through reactions catalyzed by [Ru 3 (CO) 12 ]/HBF 4 .…”

Novel iridium(III) complexes based on 2-(2,2’-bithien-5-yl)-quinoline. Synthesis, photophysical, photochemical and DFT studies

“…The synthesis of C^N cyclometalating ligands 2-(2,2'-bithien-5-yl)-4-phenylquinoline (q-bt-Ph) and 2-(2,2'-bithien-5-yl)-4-methylquinoline (q-bt-Me) was previously described [31]. Twostep synthesis of the iridium(III) complexes 1e4 is shown in Fig.…”

“…In our previous study we presented the quinoline derivatives containing the 2,2'-bithien-5-yl motif as potential candidates for cyclometalating ligands [31]. We showed the influence of substituents in the quinoline rings on their electrochemical and photophysical properties.…”