Abstract
A-π-D-π-A-based small molecules 6,6′-((thiophene-2,5-diylbis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (TDPP-T) and 6,6′-(((2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-diyl)bis(ethyne-2,1-diyl))bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione) (TDPP-EDOT) have been designed and synthesized. The diketopyrrolopyrrole acts as an electron acceptor, while the thiophene or 3,4-ethylenedioxythiophene acts as an electron donor. The donor–acceptor groups are connected by an ethynyl bridge to further enhance the conjugation. The optoelectronics, electrochemical, and thermal properties have been investigated. Organic thin film transistor (OTFT) devices prepared from TDPP-T and TDPP-EDOT have shown p-type mobility. In as cast films, TDPP-T and TDPP-EDOT have shown a hole mobility of 5.44 × 10−6 cm2 V−1 s−1 and 4.13 × 10−6 cm2 V−1 s−1, respectively. The increase in the mobility of TDPP-T and TDPP-EDOT OTFT devices was observed after annealing at 150 °C, after which the mobilities were 3.11 × 10−4 cm2 V−1 s−1 and 2.63 × 10−4 cm2 V−1 s−1, respectively.
Highlights
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Organic semiconductors have emerged as an alternative to inorganic semiconductors because of their superior advantages compared with their inorganic counterparts [1]
Tremendous work has been done by researchers on the synthesis of several small molecules and polymers constituting benzothiadiazole (BTD) [6,7,8], diketopyrrolopyrrole (DPP) [9,10,11,12], isoindigo [13,14,15], benzobisthiadiazole (BBT) [16], and arylene diimides [17,18,19], which have shown good mobility
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. For charge transfer purposes, the presence of unsaturated linkages (such as in ethylene and ethynylene) between the donor and acceptor units has been proven to be beneficial, as these linkages potentially reduce steric hindrance and enhance co-planarity along the molecular skeleton [37]. The polymeric counterpart of EDOT, i.e., poly (3, 4-ethylenedioxythiophene (PEDOT), has been extensively used for the purpose of solution processed organic electronics, while the application of EDOT is rare [39] This motivated us to apply thiiophene and 3,4-ethylenedioxythiophene as donors in small molecule-based OTFTs. TDPP-T and TDPP-EDOT (Scheme 1).
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