Oligothiophene quinoids containing a benzo[c]thiophene unit for the stabilization of the quinoidal electronic structure

Abstract

Bis(dicyanomethylene)-substituted quinoidal π-conjugated systems containing a benzo[c]thiophene unit have been investigated for application as n-type semiconductors.

Thiophene-Based Trimers and Their Bioapplications: An Overview

“…Different strategies were developed in order to obtain a trimer with a central benzo[c]thiophene unit between two thiophene units (dithienylbenzo[c]thiophene) ( Scheme 21 , I). Typically, two equivalents of 2-mercaptopyridine react with 1,2-Benzenedicarbonyl dichloride, forming two reactive thioester bonds [ 392 , 393 , 394 , 395 , 396 ]. Afterwards, the mercaptopyridines are replaced by two thiophene substituents, by addition of 2-thienylmagnesium bromide.…”

“…Afterwards, the mercaptopyridines are replaced by two thiophene substituents, by addition of 2-thienylmagnesium bromide. Finally, the central thiophene unit is obtained by employment of either phosphorous pentasulfide [ 397 , 398 ], Lawesson’s reagent [ 392 , 393 , 394 , 395 , 399 ] or Davy’s reagent [ 396 ]. Benzene-1,2-dicarbaldehyde can be used in the place of 1,2-benzenedicarbonyl dichloride: in this case 2-thienylmagnesium bromide directly reacts with the aldehyde groups, but the oxidation of the resulting alcohols to ketones is then needed before the Lawesson’s reagent step [ 400 , 401 ].…”

“…Finally, also the classic Stille or Suzuki coupling is a feasible pathway [ 390 , 404 , 408 ]. Benzene rings with a variety of substituents were introduced through those methods on the central unit of the trimers, including chloro [ 394 ], methoxyl [ 409 ], and alkyl groups [ 393 , 396 ], as well as sulfides [ 393 ], esters [ 224 ], nitriles [ 224 ], amides [ 390 , 408 ] and additional aromatic rings [ 224 , 405 , 410 ].…”

Fluorene benzothiadiazole co-oligomer based aqueous self-assembled nanoparticles

“…20 Their p-conjugated backbone commonly represents a low band gap donor-acceptor type co-oligomer by direct covalent linkage of the donor and acceptor fragment through aromatic stabilization of the quinoid structure. 21,22 The donating uorene fragment allows for a high absorption cross section and accommodates efficient through-bond energy transfer to the acceptor fragment, which results in bright chromophores that emit at long wavelengths. [23][24][25] The central p-conjugated backbone is typically anked by a combination of hydrophobic and hydrophilic sidechains.…”

Research Progress in Design, Synthesis and Application for Quinoidal Heterocyclic Compounds

“…2003 年, Frisbie 课题组 [12,13] 报道了以 3',4'-二丁基-2,2':5',2''-联三噻吩为母体的二氰 基亚甲基醌式化合物 6, 并首次将醌式噻吩化合物应用 于有机场效应晶体管中, 取得 0.02 cm 2 •V -1 •s -1 的电子 迁移率. Otsubo 课题组 [15] [20]…”