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

All‐Polymer Solar Cells: Recent Progress, Challenges, and Prospects DOI
Gang Wang, Ferdinand S. Melkonyan, Antonio Facchetti

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(13), P. 4129 - 4142

Published: Nov. 5, 2018

Abstract For over two decades bulk‐heterojunction polymer solar cell (BHJ‐PSC) research was dominated by donor:acceptor BHJ blends based on donors and fullerene molecular acceptors. This situation has changed recently, with non‐fullerene PSCs developing very rapidly. The power conversion efficiencies of have now reached 15 %, which is far above the most efficient fullerene‐based PSCs. Among various PSCs, all‐polymer cells (APSCs) donor‐polymer acceptor BHJs attracted growing attention, due to following attractions: 1) large tunable light absorption donor/polymer pair; 2) robustness film morphology; 3) compatibility scale/large area manufacturing; 4) long‐term stability external environmental mechanical stresses. Minireview highlights opportunities offered APSCs, selected families suitable for these devices optimization enhance performance further, discusses challenges facing APSC development commercial applications.

Language: Английский

Citations

522
Crystallography, Morphology, Electronic Structure, and Transport in Non-Fullerene/Non-Indacenodithienothiophene Polymer:Y6 Solar Cells DOI
Weigang Zhu, Austin P. Spencer, S. Mukherjee

et al.

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(34), P. 14532 - 14547

Published: July 23, 2020

Emerging nonfullerene acceptors (NFAs) with crystalline domains enable high-performance bulk heterojunction (BHJ) solar cells. Thermal annealing is known to enhance the BHJ photoactive layer morphology and performance. However, microscopic mechanism of annealing-induced performance enhancement poorly understood in emerging NFAs, especially regarding competing factors. Here, optimized thermal model system PBDB-TF:Y6 (Y6 = 2,2'-((2Z,2'Z)-((12,13-bis(2-ethylhexyl)-3,9-diundecyl-12,13-dihydro-[1,2,5]thiadiazolo[3,4-e]thieno[2″,3'':4',5']thieno[2',3':4,5]pyrrolo[3,2-g]thieno[2',3':4,5]-thieno[3,2-b]indole-2,10-diyl)bis(methanylylidene))bis(5,6-difluoro-3-oxo-2,3-dihydro-1H-indene-2,1-diylidene))dimalononitrile) decreases open circuit voltage (VOC) but increases short current (JSC) fill factor (FF) such that resulting power conversion efficiency (PCE) from 14 15% ambient environment. Here we systematically investigate these effects through in-depth characterizations carrier mobility, film morphology, charge photogeneration, recombination using SCLC, GIXRD, AFM, XPS, NEXAFS, R-SoXS, TEM, STEM, fs/ns TA spectroscopy, 2DES, impedance spectroscopy. Surprisingly, does not alter crystallinity, R-SoXS characteristic size scale, relative average phase purity, or TEM-imaged separation rather facilitates Y6 migration top surface, changes PBDB-TF/Y6 vertical intermixing, reduces bottom surface roughness. While increase bimolecular (BR) lower free (FC) yield, they also electron hole mobility by at least 2-fold. Importantly, increased μh dominates underlies FF PCE. Single-crystal X-ray diffraction reveals molecules cofacially pack via their end groups/cores, shortest π-π distance as close 3.34 Å, clarifying out-of-plane π-face-on molecular orientation nanocrystalline domains. DFT analysis crystals hole/electron reorganization energies low 160/150 meV, large intermolecular electronic coupling integrals 12.1-37.9 meV rationalizing 3D transport, relatively high μe 10-4 cm2 V-1 s-1. Taken together, this work clarifies richness high-efficiency NFA cells tasks for future materials design.

Language: Английский

Citations

286
High-speed sequential deposition of photoactive layers for organic solar cell manufacturing DOI
Rui Sun, Tao Wang, Xinrong Yang

et al.

Nature Energy, Journal Year: 2022, Volume and Issue: 7(11), P. 1087 - 1099

Published: Oct. 27, 2022

Language: Английский

Citations

129
Sustainable protocols for direct C–H bond arylation of (hetero)arenes DOI
Gianluigi Albano, Angela Punzi, Maria Annunziata M. Capozzi

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(5), P. 1809 - 1894

Published: Jan. 1, 2022

A comprehensive and critical overview of the sustainable strategies for direct C–H bond arylation (hetero)arenes, based on use recoverable catalysts, solvents non-conventional energy sources, has been performed.

Language: Английский

Citations

71
Recent research progress of all-polymer solar cells based on PSMA-type polymer acceptors DOI Creative Commons
Tao Wang, Mingxia Chen, Rui Sun

et al.

Chem, Journal Year: 2023, Volume and Issue: 9(7), P. 1702 - 1767

Published: June 21, 2023

Language: Английский

Citations

45
Organic solar cells based on molecular perylene diimides-type nonfullerene acceptors: achievements, challenges and the future DOI Creative Commons
Xiang Gao, Xiaojian Wu, Zhenyu Wu

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 7, 2025

Language: Английский

Citations

2
Direct C–H arylation: a “Greener” approach towards facile synthesis of organic semiconducting molecules and polymers DOI
Hassan Bohra, Mingfeng Wang

Journal of Materials Chemistry A, Journal Year: 2017, Volume and Issue: 5(23), P. 11550 - 11571

Published: Jan. 1, 2017

Direct C–H arylation enables “greener” synthesis of π-conjugated small molecules and polymers without tedious preactivation bonds.

Language: Английский

Citations

154
Direct arylation polymerization: A guide to optimal conditions for effective conjugated polymers DOI Creative Commons

Nemal S. Gobalasingham,

Barry C. Thompson

Progress in Polymer Science, Journal Year: 2018, Volume and Issue: 83, P. 135 - 201

Published: June 12, 2018

Language: Английский

Citations

134
Mesopolymer synthesis by ligand-modulated direct arylation polycondensation towards n-type and ambipolar conjugated systems DOI
Zhenjie Ni, Hanlin Wang,

Huanli Dong

et al.

Nature Chemistry, Journal Year: 2019, Volume and Issue: 11(3), P. 271 - 277

Published: Jan. 28, 2019

Language: Английский

Citations

131
Recent Advances in C–H Activation for the Synthesis of π-Extended Materials DOI
Iain A. Stepek, Kenichiro Itami

ACS Materials Letters, Journal Year: 2020, Volume and Issue: 2(8), P. 951 - 974

Published: June 29, 2020

The activation of typically unreactive aromatic C–H bonds by transition-metal catalysis has been receiving increased attention from the synthetic chemistry community in recent years. Advances this area have enabled direct and site-selective modification rings without need for pre-functionalization. Accordingly, these techniques found broad application many fields, including construction extended π-systems use materials science. This review will discuss reports reactions applied toward synthesis π-extended functional materials.

Language: Английский

Citations

109