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Impact of Chirality on Hydrogen‐Bonded Supramolecular Assemblies and Photoconductivity of Diketopyrrolopyrrole Derivatives
Author(s) -
Militzer Swann,
Nishimura Nozomi,
ÁvilaRovelo Nelson Ricardo,
Matsuda Wakana,
Schwaller Duncan,
Mésini Philippe J.,
Seki Shu,
RuizCarretero Amparo
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001540
Subject(s) - chirality (physics) , hydrogen bond , supramolecular chemistry , materials science , conjugated system , thiophene , photoconductivity , solvent , polymer , supramolecular chirality , nanotechnology , chemical physics , chemistry , organic chemistry , molecule , optoelectronics , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , composite material , quark
Abstract Hydrogen bonds can efficiently guide the self‐assembly of organic materials, enabling to tune the properties of the aggregation processes. In the case of π‐conjugated materials, several parameters such as temperature, concentration and solvent can be used to modify the aggregation state while tuning the optoelectronic properties. Chirality can be included within the impacting parameters due to the differences in molecular packing. Here, chiral and achiral thiophene‐capped diketopyrrolopyrrole derivatives were designed and synthesized containing amide bonds, with the aim to study the interplay between chiral assemblies and their stabilization through hydrogen‐bonding. Differences in aggregation properties were observed with spectroscopy and microscopy, and a contactless microwave‐based technique was used to study their intrinsic charge carrier mobility. The positive role of hydrogen‐bonding has been highlighted and the differences between chiral and achiral compounds have been elucidated.