Synthesis, Polymerization, and Unusual Properties of New Star-Shaped Thiophene Oligomers

Abstract

Terthienobenzene (TTB, 6) was prepared through a new, high yield route along with pi-extended derivatives 10 and 11. Electropolymerization of tris-EDOT derivative 11 results in a highly stable cross-linked conjugated polymer that shows polaron confinement between the TTB units as confirmed by UV-vis-NIR spectroelectrochemistry and EPR.

Electropolymerized Star-Shaped Benzotrithiophenes Yield π-Conjugated Hierarchical Networks with High Areal Capacitance

“…1c) at +0.43 V is comparably much lower than that of BTT, which is expected because of the EDOT unit substitution on the BTT core, further extending the π-conjugated motif. Here, the oxidation potential of TEBTT measured by linear scan is lower that that reported in earlier work by CV (+0.78 V; vs. Ag/AgCl) 30 . Figure 1c provides further insight on the consecutive oxidation features in TEBTT, although it should be noted that the second and third oxidation features (E ox2 = +0.71 V and E ox3 = +1.32 V) are somewhat convoluted in the broad redox response of TEBTT in this voltage window.…”

“…We also describe the experimental conditions required to form hierarchical π-conjugated frameworks with particularly high areal capacitance. Based on the basic characterization of BTT-based well-defined oligomers 28,29 and TEBTT homopolymers from previous reports, 30 we clarify the fundamental differences between electropolymerized homopolymer and copolymer networks made from these two building motifs, and emphasize their use for the synthesis of high-capacitance, nanostructured 3D polymeric networks that are resilient to repeated electrochemical cycling. In particular, comparing BTT-and TEBTT-based networks, we find that TEBTT-based homopolymers and copolymers with EDOT are substantially more capacitive (reaching up to 271.1 mF cm -2 and 443.8 mF cm -2 (1 mA cm -2 ), respectively) and stable upon cycling (up to 73%…”

Advances in Metal‐Free Heterocycle‐Based Columnar Liquid Crystals

“…Likewise, discotic compound 56 , which contains a benzotrithiophene core, was also prepared in order to fulfil similar needs in the improvement of organic electronics 74. Key intermediate benzotrithiophene triacid 54 was synthesized starting from 1,3,5‐trichlorobenzene following literature methods (Scheme ) 75. Treatment of 54 with thionyl chloride furnished the acid chloride 55 , which upon subsequent threefold amidation with 3,4,5‐tridodecyloxy aniline afforded the desired compound 56 .…”

Synthesis and characterization of fluorene tethered benzo[c]thiophene/benzo[c]selenophene analogs

“…7 Perepichka and co-workers synthesized poly star shaped tris-EDOT coupled terthienobenzene, which showed switching between red-and blue-colored stable states. 8 Now a days plenty of fluorene incorporated materials have been synthesized and used in electronic application especially ortho-linked spirobifluorene have unique photophysical properties and high triplet energy because of the p-conjugation interruption between spirobifluorene units. 9 Bao and co-workers reported the synthesis of fluorene coupled oligothiophenes as high performance semiconductors for organic thin film transistors.…”