Air-stable organic semiconductors based on 6,6′-dithienylindigo and polymers thereof

Abstract

We report on the synthesis and properties of 6,6′-dithienylindigo (DTI) and poly(DTI). Redox chemistry and ambipolar charge transport with μh = 0.11 cm2 V−1 s−1 and μe = 0.08 cm2 V−1 s−1 and excellent air stability are shown.

New core-substituted with electron-donating group 1,8-naphthalimides towards optoelectronic applications

“…[4]. In some of them the hydrogen bonds play important role in semiconducting properties [5][6]. The family of typical π-conjugated compounds is formed by the overlap of carbon p z orbitals, however, also p z orbitals of nitrogen can contribute to the conjugation [4].…”

Unusual photophysical properties of conjugated, alternating indigo–fluorene copolymers

“…23,30 Has previously reported for N,N 0 -diacylindigotins, that photoisomerization from the stable transisomers to the less-stable cis-isomers leads to the appearance of a blue-shied absorption band (with maxima in the 431-477 nm range), when compared to the trans-isomers (maxima in the 552-579 nm range). Indeed, similar absorption bands (in the 370-500 nm range) were recently observed for N,N 0 -substituted-6,6 0 -[di-(bi)thienyl]indigo oligomers and copolymers and were attributed to the loss of the H-chromophore nature of indigo (induced by the N-substitution with alkyl or acyl groups distorting the planarity of the indigo molecule), leading to the possibility of the formation of cis-indigo units and/or the existence of electronically decoupled indole-thiophene chromophores in these derivatives.…”

“…Driving organic photovoltaics (OPV) forward onto commercial products still requires further developments to be made in donor and acceptor materials, including improving their high throughput processing. [25][26][27][28][29][30] Indigo and its derivatives are long been known and used for their bright and brilliant color, as well as their high photochemical stability. [17][18][19][20][21][22] Also indigo as a "natural" dye unit has been incorporated into the backbone of such DA copolymers.…”

Rational design of bio-inspired high-performance ambipolar organic semiconductor materials based on indigo and its derivatives

“…Besides the substitutions with electron-withdrawing groups, indigoids with extended p-skeleton have also been explored recently. Glowacki and Mori groups have reported respectively that through introducing thiophene or phenyl groups at the 6,6 0 -or 5,5 0 -positions of indigo, the molecular packing fashions are transformed from twisted stacking structures to optimal parallel p-stacking structures, improving ambipolar charge-transport properties in the OFETs [29,30]. It suggests that the p-extended groups can result in the molecular packings which are more beneficial for enhancing their charge carrier mobilities.…”