High Mobility Ambipolar Diketopyrrolopyrrole-Based Conjugated Polymers Synthesized via Direct Arylation Polycondensation: Influence of Thiophene Moieties and Side Chains DOI
Yao Gao, Junhua Bai, Ying Sui

и другие.

Macromolecules, Год журнала: 2018, Номер 51(21), С. 8752 - 8760

Опубликована: Окт. 26, 2018

Seven diketopyrrolopyrrole (DPP)-based donor–acceptor (D–A) conjugated polymers, i.e., poly[2,5-bis(4-octadecyldocosyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-3,3′,4,4′-tetrafluoro-2,2′-bithiophene] (P4F2T-C40), poly[2,5-bis(4-octadecyldocosyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-1,2-bis(3,4-difluorothiophen-2-yl)ethyne] (P4FTAT-C40), poly[2,5-bis(4-octadecyldocosyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C40), poly[2,5-bis(4-tetradecyloctadecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C32), poly[2,5-bis(4-decyltetradecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C24), poly[2,5-bis(2-decyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C22), and poly[2,5-bis(2-decyltetradecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C10C12), were synthesized by direct arylation polycondensation (DArP) with multi-fluorinated thiophene derivatives 3,3′,4,4′-tetrafluoro-2,2′-bithiophene (4F2T), (E)-1,2-bis(3,4-difluorothien-2-yl)ethene (4FTVT), or 1,2-bis(3,4-difluorothiophen-2-yl) acetylene (4FTAT) as the comonomer. The structures of have a noticeable influence on optical properties self-assembly polymers. Compared to P4F2T-C40, P4FTVT-C40 showed an ∼30 nm red-shift while P4FTAT-C40 exhibited ∼60 blue-shift absorption spectrum. Top-gate bottom-contact (TGBC) organic field-effect transistors (OFETs) all polymers ambipolar transport behavior. devices based displayed poor device performance since its film was almost amorphous. In contrast, polymer 4FTVT same alkyl side chains delivered much better due crystalline nature, favorable molecular orientations, appropriate morphology. With optimized chains, P4FTVT-C32 highest hole (μh) electron mobilities (μe) ca. 2.6 8.0 cm2 V–1 s–1 in air, respectively.

Язык: Английский

Ambipolar Conjugated Polymers with Ultrahigh Balanced Hole and Electron Mobility for Printed Organic Complementary Logic via a Two‐Step CH Activation Strategy DOI
Zhenjie Ni, Hanlin Wang, Qiang Zhao

и другие.

Advanced Materials, Год журнала: 2019, Номер 31(10)

Опубликована: Янв. 17, 2019

Abstract High mobility ambipolar conjugated polymers are seriously absent regardless their great potential for flexible and printed plastic devices circuits. Here, with ultrahigh balanced hole electron developed via a two‐step CH activation strategy. Diketopyrrolopyrrole‐benzothiadiazole‐diketopyrrolopyrrole (DBD) its copolymers thiophene/selenophene units (short as PDBD‐T PDBD‐Se) used examples. PDBD‐Se exhibits highly efficient transport up to 8.90 7.71 cm 2 V −1 s in organic field‐effect transistors, presenting milestone copolymer screening. Based on this performance metrics good solubility, is investigated inkjet‐printable semiconductor ink complementary logic Under ambient processing, maximum mobilities reach 6.70 4.30 , respectively. Printed inverter NAND gates transition voltages near DD /2 fabricated, providing an easy‐handling, general material electronics logic.

Язык: Английский

Процитировано

72
Stepwise heating in Stille polycondensation toward no batch-to-batch variations in polymer solar cell performance DOI Creative Commons
Sang Myeon Lee,

Kwang Hyun Park,

Seungon Jung

и другие.

Nature Communications, Год журнала: 2018, Номер 9(1)

Опубликована: Май 8, 2018

For a given π-conjugated polymer, the batch-to-batch variations in molecular weight (M

Язык: Английский

Процитировано

71
Highly Efficient Catalysts for Direct Arylation Polymerization (DArP) DOI
Masayuki Wakioka, Fumiyuki Ozawa

Asian Journal of Organic Chemistry, Год журнала: 2018, Номер 7(7), С. 1206 - 1216

Опубликована: Май 24, 2018

Abstract Recently, the palladium‐catalyzed direct arylation polymerization (DArP) has emerged as a viable alternative to conventional synthetic means of making π‐conjugated polymers based on catalytic cross‐coupling reactions. The DArP, which proceeds through C−H bond activation, distinct advantage over in terms fewer reaction steps and higher functional group tolerance. We have developed novel catalysts for DArP by using P(2‐MeOC 6 H 4 ) 3 ( L1 P(2‐Me 2 NC L2 ligands. Although common require use strongly coordinating solvents such DMA DMF, our exhibit high activity THF toluene, are good polymers. Thus, we could realize precise synthesis highly head‐to‐tail regioregular poly(3‐hexylthiophene) (HT‐P3HT) donor–acceptor type alternating copolymers (DA polymers) with well‐controlled structures DArP.

Язык: Английский

Процитировано

69
Small Molecule Acceptor and Polymer Donor Crystallinity and Aggregation Effects on Microstructure Templating: Understanding Photovoltaic Response in Fullerene-Free Solar Cells DOI

Nicholas D. Eastham,

Alexander S. Dudnik, Thomas J. Aldrich

и другие.

Chemistry of Materials, Год журнала: 2017, Номер 29(10), С. 4432 - 4444

Опубликована: Май 3, 2017

Perylenediimide (PDI) small molecule acceptor (SMA) crystallinity and donor polymer aggregation effects on bulk-heterojunction microstructure solar cell (PSC) performance are systematically investigated. Two high-performance polymers, semicrystalline poly[5-(2-hexyldodecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione-1,3-yl-alt-4,4″dodecyl-2,2′:5′,2″-terthiophene-5,5″-diyl] (PTPD3T or D1) amorphous poly{4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl-alt-(4-(2-ethylhexyl)-3-fluorothieno[3,4-b]thiophene-2-carboxylate-2,6-diyl) (PBDTT-FTTE D2), paired with three PDI-based SMAs (A1–A3) of differing (A1 is the most, A3 least crystalline). The resulting PSC trends strikingly different from those typical fullerene-based PSCs highly material-dependent. present reflect synergistic propensities between SMA components. Importantly, active layer morphology templated by PDI in some blends others, latter largely governed aggregation. Thus, PTPD3T templating capacity increases as self-aggregation (greater Mn), optimizing A2, while A3-based cells exhibit an inverse relationship performance, which dramatically PSCs. For PBDTT-FTTE, A2-based again deliver highest PCEs ∼5%, but here both A2 PBDTT-FTTE (medium Mn) template morphology. Overall, results underscore importance nonfullerene for offer guidelines pairing acceptable polymers.

Язык: Английский

Процитировано

67
High Mobility Ambipolar Diketopyrrolopyrrole-Based Conjugated Polymers Synthesized via Direct Arylation Polycondensation: Influence of Thiophene Moieties and Side Chains DOI
Yao Gao, Junhua Bai, Ying Sui

и другие.

Macromolecules, Год журнала: 2018, Номер 51(21), С. 8752 - 8760

Опубликована: Окт. 26, 2018

Seven diketopyrrolopyrrole (DPP)-based donor–acceptor (D–A) conjugated polymers, i.e., poly[2,5-bis(4-octadecyldocosyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-3,3′,4,4′-tetrafluoro-2,2′-bithiophene] (P4F2T-C40), poly[2,5-bis(4-octadecyldocosyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-1,2-bis(3,4-difluorothiophen-2-yl)ethyne] (P4FTAT-C40), poly[2,5-bis(4-octadecyldocosyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C40), poly[2,5-bis(4-tetradecyloctadecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C32), poly[2,5-bis(4-decyltetradecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C24), poly[2,5-bis(2-decyldodecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C22), and poly[2,5-bis(2-decyltetradecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-alt-5,5′-di(thiophen-2-yl)-2,2′-(E)-1,2-bis(3,4-difluorothien-2-yl)ethene] (P4FTVT-C10C12), were synthesized by direct arylation polycondensation (DArP) with multi-fluorinated thiophene derivatives 3,3′,4,4′-tetrafluoro-2,2′-bithiophene (4F2T), (E)-1,2-bis(3,4-difluorothien-2-yl)ethene (4FTVT), or 1,2-bis(3,4-difluorothiophen-2-yl) acetylene (4FTAT) as the comonomer. The structures of have a noticeable influence on optical properties self-assembly polymers. Compared to P4F2T-C40, P4FTVT-C40 showed an ∼30 nm red-shift while P4FTAT-C40 exhibited ∼60 blue-shift absorption spectrum. Top-gate bottom-contact (TGBC) organic field-effect transistors (OFETs) all polymers ambipolar transport behavior. devices based displayed poor device performance since its film was almost amorphous. In contrast, polymer 4FTVT same alkyl side chains delivered much better due crystalline nature, favorable molecular orientations, appropriate morphology. With optimized chains, P4FTVT-C32 highest hole (μh) electron mobilities (μe) ca. 2.6 8.0 cm2 V–1 s–1 in air, respectively.

Язык: Английский

Процитировано

64