Synthesis of fluorene‐flanked diketopyrrolopyrrole‐based semiconducting polymers with thermocleavable side chains and their application in organic field effect transistors

Author:

Singh Ravinder1,Venkateswarlu Samala1,Zhong YuFang1,Li Yuning1ORCID

Affiliation:

1. Department of Chemical Engineering and Waterloo Institute for Nanotechnology (WIN) University of Waterloo Waterloo Ontario Canada

Abstract

AbstractThis study introduces the first fluorene‐flanked diketopyrrolopyrrole (FDPP)‐based semiconducting polymers, named Boc‐FDPP‐CoMs (CoM = TT or BT), synthesized via copolymerization of tert‐butoxycarbonyl (t‐Boc)‐substituted FDPP as the acceptor unit with thieno[3,2‐b]thiophene (TT) or bithiophene (BT) as the donor comonomers. The incorporation of t‐Boc groups addresses challenges related to poor solubility and polymer backbone twisting associated with the FDPP building block. While Boc‐FDPP‐CoMs demonstrate solubility in common organic solvents, facilitating favourable solution‐processability for uniform film fabrication, they exhibit significant backbone twisting, leading to poor charge transport properties. Post‐deposition thermal annealing at a mild temperature as low as 170°C conveniently removes t‐Boc groups. The resulting t‐Boc‐free copolymers, NH‐FDPP‐TT and NH‐FDPP‐BT, exhibit hole mobilities up to 5.0 × 10−3 and 2.2 × 10−3 cm2 V−1 s−1 in organic field effect transistors (OFETs), respectively, representing a substantial increase compared to their counterparts with t‐Boc groups. This study underscores a meticulously designed strategy for achieving solution solubility and backbone coplanarity through side‐chain engineering for FDPP and potentially other sterically demanding building blocks to construct high‐performance semiconducting polymers for OFETs and other applications.

Funder

Natural Sciences and Engineering Research Council of Canada

Publisher

Wiley

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1. Preface to the Organic and Printed Electronics Special Issue Section;The Canadian Journal of Chemical Engineering;2024-08-28

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