Issue 17, 2016

Monodisperse macromolecules based on benzodithiophene and diketopyrrolopyrrole with strong NIR absorption and high mobility

Abstract

A series of monodisperse macromolecules with A2–A1–D–A1–A2 structure based on benzodithiophene (BDT) and diketopyrrolopyrrole (DPP) BDT-4DPP, BDT-DPP-Rhod and BDT-DPP-CA were designed, theoretically calculated and synthesized, and compared with their parent molecules BDT-2DPP and BDTS-2DPP with A1–D–A1 structure. These molecules possessed highly planar molecular geometries and high crystallinity. These molecules exhibited good thermal stability with decomposition temperatures of 322–388 °C, strong visible and near-infrared absorption (500–1000 nm), and HOMO energy levels of −5.38 to −5.19 eV and LUMO energy levels of −3.69 to −3.46 eV. Relative to the parent molecules A1–D–A1, A2–A1–D–A1–A2 molecules exhibited red-shifted and stronger absorption. The charge transport properties of these molecules were investigated by organic field-effect transistors, and their hole mobilities were 0.036–1.12 cm−2 V−1 s−1. Replacing alkyl with alkylthio on BDT led to mobility enhancement by one order of magnitude.

Graphical abstract: Monodisperse macromolecules based on benzodithiophene and diketopyrrolopyrrole with strong NIR absorption and high mobility

Supplementary files

Article information

Article type
Paper
Submitted
31 Oct 2015
Accepted
11 Dec 2015
First published
14 Dec 2015

J. Mater. Chem. C, 2016,4, 3781-3791

Monodisperse macromolecules based on benzodithiophene and diketopyrrolopyrrole with strong NIR absorption and high mobility

J. Wang, K. Shi, Y. Suo, Y. Lin, G. Yu and X. Zhan, J. Mater. Chem. C, 2016, 4, 3781 DOI: 10.1039/C5TC03589A

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