Conjugated Random Donor–Acceptor Copolymers of [1]Benzothieno[3,2-b]benzothiophene and Diketopyrrolopyrrole Units for High Performance Polymeric Semiconductor Applications

Abstract

Three-component random copolymers having different ratios of [1]­benzothieno­[3,2-b]­benzothiophene (BTBT) and diketopyrrolopyrrole (DPP) units were synthesized, and their application in organic field effect transistors (OFET) has been discussed. These low band gap polymers exhibit p-type semiconducting properties, and it has been observed that increase in the percentage composition of the fused chalcogenophene (BTBT) in the polymer backbone significantly improves the charge carrier mobility (μh) up to 2.47 cm2 V–1 s–1. The GIXRD technique and AFM have been used to explain the influence of BTBT on the nature of molecular packing in the polymer thin films. These results unveil the role of the effective conjugation length as well as the intermolecular ordering of the polymer chains on the charge carrier transport in OFET.

Conjugated D–A terpolymers for organic field-effect transistors and solar cells

“…We, along with Ajayaghosh et al 32 , introduced benzothieno[3,2-b]benzothiophene (BTBT) into DPP-thiophene and DPP-bithiophene polymers. BTBT and its derivatives are typical small organic semiconductors with high charge mobilities.…”

Synthesis and characterization of semiaromatic polyamides comprising benzofurobenzofuran repeating units

“…A second, major decomposition step was observed at temperatures above 400°C in air. Fused benzothiophenes have recently been shown to exhibit excellent semiconducting properties, [9][10][11][12][13][14][15][16] while organic semiconductors based on related benzofurans have more recently been reported, as well. 20,21 Therefore, the structural similarity of the benzofurobenzofuran core to benzothienobenzothiophene (BTBT) indeed called for an investigation of the optoelectronic properties of films of the benzofurobenzofuran polyamide PA6B as well as the corresponding dicarboxamide model compound 7.…”

“…[9][10][11][12] Significant efforts have been devoted to investigating the correlation between the chemical structure, morphology, and electronic properties of BTBT-based materials, [13][14][15] including the incorporation of BTBT units into polymer semiconductors that exhibited high charge carrier mobilites. 16 However, polyamides comprising repeating units based on either BTBT or its oxygen-analogue BFBF have not previously been reported. Different from BTBT derivatives, the benzofurobenzofuran core is readily accessible in larger quantities via its dihydro-derivatives that, in turn, can be straightforwardly synthesized in an acid-catalyzed condensation reaction of glyoxal derivatives with a variety of p-substituted phenols.…”

An A‐D‐A′‐D‐A Conjugated Molecule Entailing Diazapentalene Unit for an n‐Type Organic Semiconductor

“…The past decades have witnessed the significant progresses of organic and polymeric semiconductors. [1][2][3][4][5] Various conjugated frameworks, such as diketopyrrolopyrrole (DPP), [6][7][8][9][10][11][12][13][14][15] naphthodithiophenediimide (NDTI), [16][17][18][19][20][21][22][23] benzodifurandione-based oligo(p-phenylene vinylene) (BDOPV) [24] and isoindigo, [25][26][27][28] have been explored to construct the conjugated molecules and polymers for semiconductors of high charge mobilities. For instance, the electron deficiency,p lanar conjugated structure and easyf unctionalizatione nableD PP as av ersatile building block for organic and polymerics emiconductors.…”