Hexaarylbenzene based high-performance p-channel molecules for electronic applications

Abstract

The latest progress on semiconducting applications of hexaarylbenzene is reviewed, including a fundamental overview of geometry, synthetic methods, structure-property relationship, design strategies and electronic applications in OFET, OLED and OPV.

Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties

“…Similar to the change in Stokes shift of 4e from 86 to 128 nm ( 5e ), solution QY of 4e increased from around 30% to around 70% ( 5e ), suggesting the electron-donating and charge transfer effects of 4,4′-dimethoxytriphenylamine. Considering all quantum yield comparisons, excellent solution quantum yields reaching up to 97% ( 4a ) were achieved, outperforming many fluorescent luminophores available in the literature. − Moreover, with the change of electron-withdrawing and -donating substituents, significant changes in the fluorescence colors of 4a–e and 5a–e were observed in THF, which ranged from greenish to dark blue, shifting from 523 to 418 nm with 4a–e and from orange to sky blue, shifting from 556 to 469 nm with 5a–e , respectively (Figure ). While a combination of 4-CNPh (strong electron-withdrawing group)-substituted TT and 4,4′-dimethoxytriphenylamine produced an orange color ( 5a ), combination of C 6 H 13 (weak electron donor)-substituted TT and triphenylamine ( 4e ) gave a dark blue color.…”

Ionomer Membranes Produced from Hexaarylbenzene-Based Partially Fluorinated Poly(arylene ether) Blends for Proton Exchange Membrane Fuel Cells

“…IEC indicates the sulfonic acid concentration [−SO 3 H] in standardized matrix. The structure of an HAB derivative with unique stereospecific features can effectively provide a dense sulfonation feature that facilitates conduction [47,48]. Typically, as the IEC of a PEM increases, the resulting hydrogen bonding forces make the membrane more hygroscopic and susceptible to moisture plasticization effects.…”

“…This study performed dense sulfonation by using trifluoromethyl (−CF 3 ) structures designed for poly(arylene)s to fabricate ready-blended polymer PEMs. The strategy used in this study involved combining a fluorenyl with a cardo structure [46], high torsional orientation, and highly rigid hexaarylbenzene (HAB) derivatives [47] with sulfonated poly(arylene)s. The structures produced through this strategy were expected to exhibit a large proton transport space and appropriate mechanical and thermal stability. To investigate and explain the separation of ionomer blends, it is necessary to have proper conditions in processes.…”

Programmed Synthesis of Tetra-Aryl Thiophenes with Stepwise, Ester-Controlled Regioselectivity

“…Arylated thiophene analogues are recognized building blocks in drug discovery, with derivatives used as estrogen receptor agonists 1 and A1 adenosine receptor agonists, 2 antitumor agents, 3−5 antimicrobial agents, 6,7 as well as tyrosine phosphatase inhibitors, 8 bacterial DNA gyrase inhibitors, 9 and 15-lipoxygenase-1 inhibitors, 10 among other applications. 11−13 Tetra-aryl thiophenes, in particular, have emerged as compounds of interest for optoelectronic materials, 14−20 energy storage, 21 precursors to hexaarylbenzene p-channels, 22,23 and polymeric materials. 24−26 Currently, however, the range of methodologies for the complete and selective arylation of thiophenes is limited.…”

“…Multi-arylated thiophenes have become ubiquitous motifs in a number of salient industries in the last two decades. Arylated thiophene analogues are recognized building blocks in drug discovery, with derivatives used as estrogen receptor agonists and A1 adenosine receptor agonists, antitumor agents, − antimicrobial agents, , as well as tyrosine phosphatase inhibitors, bacterial DNA gyrase inhibitors, and 15-lipoxygenase-1 inhibitors, among other applications. − Tetra-aryl thiophenes, in particular, have emerged as compounds of interest for optoelectronic materials, − energy storage, precursors to hexaarylbenzene p -channels, , and polymeric materials. − Currently, however, the range of methodologies for the complete and selective arylation of thiophenes is limited. In order to efficiently access this promising class of molecules, and further expand the range of applications, we report herein a programmed methodology for the regioselective synthesis of tetra-aryl thiophenes.…”