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

et al.

Chemistry of Materials, Journal Year: 2017, Volume and Issue: 29(10), P. 4432 - 4444

Published: May 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.

Language: Английский

Robust Direct (Hetero)arylation Polymerization in Biphasic Conditions DOI

François Grenier,

Karine Goudreau,

Mario Leclerc

et al.

Journal of the American Chemical Society, Journal Year: 2017, Volume and Issue: 139(7), P. 2816 - 2824

Published: Jan. 26, 2017

The synthesis of conjugated polymers from direct (hetero)arylation polymerization (DHAP) has been achieved for the first time using biphasic water/toluene conditions. This protocol is robust enough to form even when air introduced in system. General reactivity demonstrated a single set conditions with thienyl- or phenyl-based substrates, whether they are electron-rich electron-poor. Complete characterization differential scanning calorimetry and 1H NMR UV-vis-NIR spectroscopies presented, demonstrating this DHAP offers comparable better properties than very best values published thus far. High molecular weights obtained, showcasing perfect equilibrium selectivity attained method. Moreover, efficient versatile methodology, which also uses low-cost, "wet" reagents, scalable done at ambient pressure.

Language: Английский

Citations

76
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

et al.

Advanced Materials, Journal Year: 2019, Volume and Issue: 31(10)

Published: Jan. 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.

Language: Английский

Citations

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

et al.

Nature Communications, Journal Year: 2018, Volume and Issue: 9(1)

Published: May 8, 2018

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

Language: Английский

Citations

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

Asian Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 7(7), P. 1206 - 1216

Published: May 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.

Language: Английский

Citations

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

et al.

Chemistry of Materials, Journal Year: 2017, Volume and Issue: 29(10), P. 4432 - 4444

Published: May 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.

Language: Английский

Citations

67