2,9-Dibenzo[b,def]chrysene as a building block for organic electronics

Abstract

A new series of three donor–acceptor conjugated polymers based on a low-cost, easily accessible vat dye called Vat orange 1 have been prepared. The polymers have bandgap values ranging from 1.61 to 1.86 eV.

Direct C–H electrophilic borylation with (C6F5)2B–NTf2 to generate B–N dibenzo[a,h]pyrenes

“…The parent all carbon dibenzo[ a , h ]pyrene unit is related to the base structure of the commercially available orange dye Vat Orange 1, which has recently been incorporated into donor–acceptor π-conjugated polymers for use in organic electronic devices. 47 To our knowledge, no BN doped versions of this framework have been reported.…”

Industrial vat orange dyes for organic field effect transistors

“…The large and flat p surface of the three investigated dyes reduces the solubility in common organic solvents but does not impede their processing via physical vapor deposition. Among them, vat orange 1 and vat orange 3 either in their pristine form or as various derivatives 78,79 have been so far the focus of several investigations because of their charge transport in OFETs, [80][81][82] organic photovoltaics 78,83,84 or electrochemical energy storage 85 fields. A recent review article by Jean-François Morin summarizes in fact the entire effort made by the scientific community in the field of vat dye derivatization for organic electronic applications.…”

6H-[1,2,5]Thiadiazolo[3,4-e]thieno[3,2-b]indole-flanked para-azaquinodimethane based aromatic-quinoidal polymer semiconductors with high molecular weights synthesized via direct arylation polycondensation

“…[29][30][31][32][33] As a linked unit in the conjugated polymer, replacing the single thiophene ring with the fused heteroaromatic ring endows the resulting polymer with tunable physicochemical and semiconducting properties. [34][35][36] For example, introducing the benzo[c] [1,2,5]thiadiazole unit into a thiopheneflanked p-AQM polymer backbone offers improved backbone rigidity, stronger intermolecular interactions, and higher crystallinity, endowing the resulting polymer with high hole transport mobility. 37 Therefore, the introduction of the fused heteroaromatic rings in p-AQMs may further expand the molecular design strategies of p-AQM-based conjugated polymers.…”