An ester functionalized wide bandgap polythiophene for organic field-effect transistors

Gamage, Prabhath L.; Gunawardhana, Ruwan; Bulumulla, Chandima; Kularatne, Ruvanthi N.; Gedara, Chinthaka M. Udamulle; Ma, Ziyuan; Stefan, Mihaela C.

doi:10.1016/j.synthmet.2021.116767

Cited by 3 publications

(5 citation statements)

References 43 publications

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“…17,48,63,69 In agreement with the most widely studied low bandgap polythiophene derivatives, such as P3HTh, PTB7-Th, or extensive thiophene-based polymers, these new o-AZdANThs are slightly low bandgap materials. 41,62,63 The results of this works show differences in the optoelectronic properties between the synthesized oligomers and some low bandgap polythiophene derivatives (Table 4 and Fig. 10).…”

Section: Polymer Chemistry Papermentioning

confidence: 82%

Section: Resultsmentioning

confidence: 99%

“…In this way, it could to obtain processable materials in solution, and simultaneously with improved electronic properties to access new or better configurations in optoelectronic devices. 55,62,63 In the case of o-AZdAN2Th, the suitable optoelectronic properties together with its high thermal stability, would allow to think about future works using this Schiff base oligomer as active layer or complementary material for PSCs using fullerene derivatives such as PC 71 BM or non-fullerene materials as acceptor materials. 17,47,55…”

Section: Polymer Chemistry Papermentioning

confidence: 99%

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Thiophene- and bithiophene-based π-conjugated Schiff base oligomers containing binaphthalene moieties in the backbone. Properties and computational simulations

González,

Mariman,

Hauyon

et al. 2024

Polym. Chem.

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Section: Polymer Chemistry Papermentioning

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Section: Polymer Chemistry Papermentioning

confidence: 99%

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Thiophene- and bithiophene-based π-conjugated Schiff base oligomers containing binaphthalene moieties in the backbone. Properties and computational simulations

González,

Mariman,

Hauyon

et al. 2024

Polym. Chem.

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“…Heteropentalenes are an important family of heterocyclic compounds frequently used as building blocks for organic semiconducting materials (OSMs) . Among the heteropentalenes, thieno[3,2- b ]thiophene is the “star” molecule, which is employed as a donor unit in organic semiconducting polymers, such as PDPP-TT (poly[2,5-(2-octyldodecyl)-3,6-diketopyrrolopyrrole- alt -5,5-(2,5-di(thien-2-yl)thieno [3,2 -b ]-thiophene)]), which has been used in organic field-effect transistors (OFETs), − and polycyclic ring systems, such as ITIC (3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)-indanone))-5,5,11,11-tetrakis(4-hexylphenyl)-dithieno[2,3- d :2,3′- d′ ]- s -indaceno[1,2- b :5,6- b′ ]dithiophene) derivatives − and Y-series non-fullerene small molecular acceptors used in organic photovoltaics (OPVs). − In recent decades, there has been significant interest in organic electronics, including but not limited to OFETs, OPVs, and organic light-emitting diodes (OLEDs). − Of particular importance in this area of research is the reduction of the band gap of organic semiconductors, which enhances both charge-transfer and optical absorption characteristics. This narrowing of the band gap leads to a redshift in the absorption of light by the semiconductor, thereby increasing the efficiency of solar energy absorption …”

Section: Introductionmentioning

confidence: 99%

Chalcogenopheno[3,2-b]pyrrole-Containing Donor–Acceptor–Donor Organic Semiconducting Small Molecules for Organic Field-Effect Transistors

Ma,

Udamulle Gedara,

Wang

et al. 2023

ACS Appl. Mater. Interfaces

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A group of chalcogenopheno[3,2-b]pyrroles, including thieno[3,2-b]pyrrole (TP), furo[3,2-b]pyrrole (FP), and selenopheno[3,2-b]pyrrole (SeP), and thieno[3,2-b]thiophene (TT) electron-donating units were coupled with a thiophene-flanked diketopyrrolo[3,4-c]pyrrole (ThDPP) acceptor to generate four donor–acceptor–donor (D-A-D) semiconducting small molecules (ThDPP-TT, ThDPP-FP, ThDPP-TP, and ThDPP-SeP). This study systematically investigated the differences between chalcogenopheno[3,2-b]pyrroles and TT. From the characterizations, chalcogenopheno[3,2-b]pyrrole-containing molecules showed lower band gaps and binding-energy cold crystallization behavior. The enthalpies of cold crystallization were correlated with the weight of the chalcogen in ThDPP-FP, ThDPP-TP, and ThDPP-SeP, which were evaluated as intermolecular chalcogen-bond interactions between chalcogen and pyrrole nitrogen in chalcogenopheno[3,2-b]pyrroles. A stronger chalcogen bond interaction resulted in stronger self-aggregation in thin films with thermal treatment, which resulted in a polycrystalline structure in chalcogenopheno[3,2-b]pyrrole-containing molecules. For the application in an organic field-effect transistor, all four molecules showed good performance with the highest hole mobilities as 6.33 × 10–3 cm2 V–1 s–1 for ThDPP-TT, 2.08 × 10–2 cm2 V–1 s–1 for ThDPP-FP, 1.87 × 10–2 cm2 V–1 s–1 for ThDPP-TP, and 6.32 × 10–3 cm2 V–1 s–1 for ThDPP-SeP, and the change of mobility is well correlated to the root-mean-square roughness of the thin films. Overall, all the chalcogenopheno[3,2-b]pyrrole-containing molecules showed lower band gaps, polymorphism, and better charge transport properties compared to TT-containing molecules, which motivates replacing TT with chalcogenopheno[3,2-b]pyrroles in conjugated polymers, non-fullerene small molecular acceptors, and narrow-band-gap donors.

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“…Organic semiconducting materials (OSMs) gained attention within the last few decades due to their relatively low cost, light weight, flexibility, and tunable optoelectronic properties. − OSMs are used in organic field-effect transistors (OFETs), light-emitting diodes, solar cells, photodetectors, memory devices, chemical sensors, logic circuits, etc . Among organic electronic devices, OFETs are essential components in analog and digital integrated circuits. − OSMs are categorized into two types depending on their molecular backbone structure and molecular weight: small organic semiconducting molecules and semiconducting polymers.…”

Section: Introductionmentioning

confidence: 99%

Siloxane Side-Chain-Modified Diketopyrrolopyrrole and Thienopyrrole Containing Small Molecules for Organic Field-Effect Transistors

Gedara

Talukder

et al. 2022

ACS Appl. Electron. Mater.

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Thieno[3,2-b]pyrrole (TP) is a donor moiety employed in organic semiconducting small molecules and polymers. Among the TP-containing small molecules reported, benzo[c][1,2,5]thiadiazole (BT) acceptor-based donor–acceptor (DA) type molecules have shown mobilities of ∼0.1 cm2 V–1 s–1. In this study, we are reporting the synthesis, characterization, and testing of the organic field-effect transistor (OFET) performance of two donor–acceptor–donor (DAD) type small molecules with TP donors and siloxane-functionalized diketopyrrolopyrrole (DPP) acceptors, namely, diethyl 2,2′-((2,5-bis(6-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)hexyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thiophene-5,2-diyl))bis(4-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (DPP-2T-2TP) and diethyl 2,2′-((2,5-bis(6-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)hexyl)-3,6-dioxo-2,3,5,6 tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(furan-5,2-diyl))bis(4-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (DPP-2F-2TP). The difference between DPP-2T-2TP and DPP-2F-2TP is the spacer between the donor and acceptor. According to a few reports, siloxane-containing side chains were known to provide stability in ambient conditions in OFETs compared to their alkyl-substituted analogs. In this study, siloxane side-chain-substituted small molecular OFETs were fabricated, annealed, and tested under ambient conditions. Both molecules showed OFET activity with a maximum hole mobility of 4.10 × 10–2 cm2 V–1 s–1 (DPP-2T-2TP) and 6.40 × 10–5 (DPP-2F-2TP) cm2 V–1 s–1 in ambient conditions, where thiophene spacer containing DPP-2T-2TP had a better performance.

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An ester functionalized wide bandgap polythiophene for organic field-effect transistors

Cited by 3 publications

References 43 publications

Thiophene- and bithiophene-based π-conjugated Schiff base oligomers containing binaphthalene moieties in the backbone. Properties and computational simulations

Thiophene- and bithiophene-based π-conjugated Schiff base oligomers containing binaphthalene moieties in the backbone. Properties and computational simulations

Chalcogenopheno[3,2-b]pyrrole-Containing Donor–Acceptor–Donor Organic Semiconducting Small Molecules for Organic Field-Effect Transistors

Siloxane Side-Chain-Modified Diketopyrrolopyrrole and Thienopyrrole Containing Small Molecules for Organic Field-Effect Transistors

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