Efficient Tin-Free Route to a Donor-Acceptor Semiconducting Copolymer with Variable Molecular Weights / Tkachov Roman,Karpov Yevhen,Senkovskyy Volodymyr,Raguzin Ivan,Zessin Jakob,Lederer Albena,Stamm Manfred,Voit Brigitte,Beryozkina Tetyana,Bakulev Vasiliy,Zhao Wei,Facchetti Antonio,Kiriy Anton // MACROMOLECULES. - 2014. - V. 47, l. 12. - P. 3845-3851.

ISSN/EISSN:

0024-9297 / 1520-5835

Type:

Article

Abstract:

For the fabrication of efficient photovoltaic devices and thin-film transistors, pi-conjugated polymers with high molecular weight are desirable as they frequently show superior charge transport, morphological, and film-forming properties. Herein, we present an extremely fast tin-free method to polymerize a naphthalene diimide-dithiophene-based anion-radical monomer in the presence of Pd catalyst having bulky and electron-rich tritert-butylphosphine ligands (Pd/(PBu3)-Bu-t). With this method, the corresponding semiconducting polymer, PNDIT2 (also known as P(NDI2OD-T2 or N2200) with a molecular weight in excess of 1000 kg/mol can be obtained quickly at room temperature and at rather low catalyst concentrations. In general, molecular weights of resulting polymer can be regulated by reaction conditions (e.g., catalyst concentration and reaction time). Besides high molecular weight PNDIT2 (e.g., with M-N similar to 350 kg/mol, D-M =2.9), PNDIT2 with moderate molecular weight (e.g., M-N similar to 110 kg/mol, D-M = 2.3) and low molecular weight (e.g., M-W similar to 12 kg/mol, D-M = 1.9), can also be obtained. It was found that thus-prepared PNDIT2 exhibits field-effect electron mobilities of up to similar to 0.31 cm(2)/(V s), similar to the Stille-derived N2200 control polymer (up to similar to 0.33 cm(2)/(V s)). Preliminary studies demonstrated that Pd/(PBu3)-Bu-t catalyst is remarkably efficient in polymerizing of other anion-radical monomers, such as isoindigo-, and diketopyrrolopyrrole-based ones, although conventional Ni and Pd catalysts (e.g., Ni(dppp)Cl-2, Ni(dppp)Cl-2, Pd(PPh3)(4)) failed to polymerize these monomers.

Author keywords:

FIELD-EFFECT TRANSISTORS; CHAIN-GROWTH POLYCONDENSATION; POLYMER SOLAR-CELLS; HIGH-MOBILITY; N-CHANNEL; SUZUKI POLYCONDENSATION; ORGANIC TRANSISTORS; PRINTED TRANSISTORS; ELECTRON-TRANSPORT; PERFORMANCE

DOI:

10.1021/ma5007667

Web of Science ID:

ISI:000338089400011

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JUN 24
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
EISSN	1520-5835
Keywords-Plus	FIELD-EFFECT TRANSISTORS; CHAIN-GROWTH POLYCONDENSATION; POLYMER SOLAR-CELLS; HIGH-MOBILITY; N-CHANNEL; SUZUKI POLYCONDENSATION; ORGANIC TRANSISTORS; PRINTED TRANSISTORS; ELECTRON-TRANSPORT; PERFORMANCE
Research-Areas	Polymer Science
Web-of-Science-Categories	Polymer Science
Author-Email	a-facchetti@northwestern.edu kiriy@ipfdd.de
ResearcherID-Numbers	Voit, Brigitte/D-4755-2009 Umlauf, Ursula/D-3356-2014 Lederer, Albena/A-6426-2011
ORCID-Numbers	Voit, Brigitte/0000-0002-4531-691X
Funding-Acknowledgement	German Excellence Initiative via the Cluster of Excellence ``Center for Advancing Electronics Dresden{''} (cfAED) {[}EXC 1056]; DFG {[}KI-1094/4]
Funding-Text	We gratefully acknowledge support from the German Excellence Initiative via the Cluster of Excellence EXC 1056 ``Center for Advancing Electronics Dresden{''} (cfAED) and DFG (SPP 1355 ``Elementary Processes of Organic Photovoltaics{''
Number-of-Cited-References	58
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	71
Journal-ISO	Macromolecules
Doc-Delivery-Number	AK0FX