3001-15-8Relevant articles and documents
Conveniently Synthesized Butterfly-Shaped Bitriphenylenes and their Application in Solution-Processed Organic Field-Effect Transistor Devices
Chennamkulam, Ajith Mithun,Dutta, Soumya,Karunakaran, Logesh,Paneer, Shyam Vinod Kumar,Ramakrishna, Jagarapu,Subramanian, Venkatesan,Venkatakrishnan, Parthasarathy
, (2019)
Various π-extended new bitriphenylene derivatives (both conformationally-free and conformation-locked) have been successfully synthesized by a facile Scholl oxidative cyclodehydrogenation method in good to excellent yields. Their optical properties in solution and film states reveal possibility for self-ordering. The molecular packing in solid-state demonstrates favorable π–π stacking as well as weak intermolecular interactions leading to face-to-face or slipped-stack arrangements. Besides, these butterfly-shaped large bitriphenylenes display near-UV absorption, excellent photochemical, thermal, and electrochemical stabilities. The all-organic anneal-free transparent FETs fabricated from solution-processable bitriphenylenes showcase significant improvement (ca. 4 orders of magnitude higher) in charge transporting abilities (μh: from ca. 10–7 to 10–3 cm2/(Vs)) when compared to model triphenylene. The fabricated FETs unveil excellent air stability (> 1 year under atmospheric conditions) highlighting the utility of these novel link-locked triphenylene skeletons in organic electronics.
Synthesis, characterization, and systematic structure–property investigation of a series of carbazole–thiophene derivatives
Damit,Nordin,Ariffin,Sulaiman
, p. 1800 - 1812 (2017)
A series of carbazole–thiophene oligomers linked at the 3,6-positions of the carbazole fragment of 4,4′-bis(carbazol-9-yl)biphenyl (CBP) and 4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl (CDBP) with systematically elongated molecular lengths were synthesized via the Suzuki–Miyaura and Ullmann coupling reactions. Their electronic properties were studied by UV-Vis, cyclic voltammetry, and theoretical calculations. The coupling of CBP and CDBP with thiophene and bi- and terthiophene residues stabilized the HOMO and LUMO energy levels. The absorption and emission spectra exhibited a gradual red shift. The compounds with oligothiophene units had greatly decreased band gaps compared with CBP and CDBP. Therefore, these units may be introduced into the backbone of π-conjugated small molecules to develop new materials with low band gaps that may have potential applications in optoelectronics.
Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone
Xia, Hongyu,Wang, Ganghu,Zhao, Dongbo,Zhu, Chunyin
supporting information, p. 922 - 929 (2022/02/10)
A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w
"benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers
Minus, Matthew B.,Moor, Sarah R.,Pary, Fathima F.,Nirmani,Chwatko, Malgorzata,Okeke, Brandon,Singleton, Josh E.,Nelson, Toby L.,Lynd, Nathaniel A.,Anslyn, Eric V.
supporting information, p. 2873 - 2877 (2021/05/05)
Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.
