Performance Comparisons of Polymer Semiconductors Synthesized by Direct (Hetero)Arylation Polymerization (DHAP) and Conventional Methods for Organic Thin Film Transistors and Organic Photovoltaics.

Arthur D Hendsbee,Yuning Li

doi:10.3390/molecules23061255

Arthur D Hendsbee, Yuning Li

Open Access

https://doi.org/10.3390/molecules23061255

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Journal: Molecules (Basel, Switzerland)	Publication Date: May 24, 2018
Citations: 22	License type: CC BY 4.0

Affiliation: University of Waterloo

Abstract

C-C bond forming reactions are central to the construction of π-conjugated polymers. Classical C-C bond forming reactions such as the Stille and Suzuki coupling reactions have been widely used in the past for this purpose. More recently, direct (hetero)arylation polymerization (DHAP) has earned a place in the spotlight with an increasing number of π-conjugated polymers being produced using this atom-economic and more sustainable chemistry. As semiconductors in organic electronics, the device performances of the polymers made by DHAP are of great interest and importance. This review compares the device performances of some representative π-conjugated polymers made using the DHAP method with those made using the conventional C-C bond forming reactions when they are used as semiconductors in organic thin film transistors (OTFTs) and organic photovoltaics (OPVs).

Highlights

Organic electronics enabled by polymer semiconductors is an exciting field of research that promises to pave the way for low-cost, flexible electronic devices such as organic thin film transistors (OTFTs) [1,2] and organic photovoltaics (OPVs) [3,4]
Directarylation polymerization (DHAP) of a halogenatedaryl compound with anotheraryl compound possessing activated C-H bonds has emerged as an alternative approach to the conventional C-C bond formation methods such as Stille and Suzuki coupling polymerization for the synthesis of linear π-conjugated polymers
Since direct (hetero)arylation polymerization (DHAP) does not require the use of aaryl compound possessing a reactive directing group such as an organostannyl group in the case of a Stille coupling polymerization, fewer steps are needed for DHAP, which can improve the atom economy and reduce the cost for the synthesis of conjugated polymers

Summary

Introduction

Organic electronics enabled by polymer semiconductors is an exciting field of research that promises to pave the way for low-cost, flexible electronic devices such as organic thin film transistors (OTFTs) [1,2] and organic photovoltaics (OPVs) [3,4]. Common methods for the C-C bond formation, such as Stille and Suzuki coupling reactions require an aryl halide and an aromatic compound with a reactive directing group, e.g., a boronic acid (or ester) for the Suzuki coupling and an organostannyl group for the Stille coupling These reactions, while highly effective in C-C bond formation, require additional steps to install the directing groups, which increases the production cost and generates stoichiometric amounts. To address issues groups, associated with the common synthetic used to prepare polymer install these the directing which increases the production cost methods and generates stoichiometric semiconductors, C-C bond the so-called direct (hetero) amounts aofnovel by-products that areforming potential methodology, health and environmental hazards. In the past few years, rigorous studies have been better understanding of the DHAP mechanism, a number of high-quality polymer semiconductors conducted to optimize the synthetic conditions to minimize or eliminate these side reactions. Direct (hetero)arylation polymerization of a 2-bromo-3-alkylthiophene, showing the potential for forming homocoupling and branching defects.

Polymer Semiconductors for Organic Thin Film Transistors

Transfer

Polymer Semiconductors for Organic Photovoltaics

Findings

Conclusions