Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state

Kun Yang, Xiang Li, Yi Fan Huang, Ram S. Bhatta, Jiawei Liu, Mesfin Tsige, Chien-Lung Wang, Stephen Z.D. Cheng, Yu Zhu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Two diketopyrrolopyrrole (DPP)-based donor-acceptor oligomers with thermal labile 2-methylhexyl-2-oxylcarbonyl (mHoc) groups, mHocPBT and mHocTBT, were synthesized and characterized to study the hydrogen-bonding mediated molecular packing in solid state. The soluble oligomers can be converted to strong intermolecular hydrogen-bonded and pigment-like materials HPBT and HTBT by annealing the casted solid film at a temperature between 180 and 200 °C. The formation of intermolecular hydrogen bonding significantly altered the conformation of the molecules, molecular packing structure and related optical properties of the oligomers, with HPBT molecule exhibiting bathochromic shift and HTBT molecule exhibiting hypsochromic shift on UV/Vis spectra. Spin-casted mHocTBT and HTBT films also exhibited interesting morphology and charge transport properties. Even though the single mHocTBT oligomer molecule has a better coplanar molecular conformation as compared with that of HTBT, an enhanced π-π stacking structure and larger crystal grain size rendered HTBT film better charge transport performance.

Original languageEnglish
Pages (from-to)238-245
Number of pages8
Journalpolymer
Volume160
DOIs
StatePublished - 3 Jan 2019

Keywords

  • Conjugated molecules
  • Hydrogen bond
  • Molecular packing

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