Abstract
Among recent advances toward efficient semiconducting materials, rational design guidelines have emerged focusing on the synergy between various intermolecular interactions to improve the solid-state order of π-conjugated molecules in organic electronic devices. Herein, we focus our attention on halogen bonding (XB) interactions and the crucial role of electron withdrawing substituents (e.g., nitro and fluoro) toward influencing solid-state properties via secondary interactions. Employing iodoethynyl benzene derivatives (F2BAI and (NO2)2BAI) and thiophene/furan-based building blocks equipped with pyridyl groups as self-assembling domains (PyrTF and PyrT2), co-crystals driven by XB, and π-stacking interactions were formed and studied. Spectroscopic and thermal analysis of 1:1 mixture provides initial evidence of co-crystallization. X-ray crystallography affords the inherent solid-state packing motifs within each assembly. Computational studies support experimental observations, revealing the dominant interactions and contribution of each substituent group toward increasing the stability of the resulting assemblies.
Recommended Citation
S. T. Nguyen et al., "Elucidating the Effects of Fluoro and Nitro Substituents on Halogen Bond Driven Assemblies of Pyridyl-Capped Π-Conjugated Molecules," Crystal Growth and Design, vol. 16, no. 11, pp. 6648 - 6653, American Chemical Society, Nov 2016.
The definitive version is available at https://doi.org/10.1021/acs.cgd.6b01321
Department(s)
Chemistry
International Standard Serial Number (ISSN)
1528-7505; 1528-7483
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2024 American Chemical Society, All rights reserved.
Publication Date
02 Nov 2016
Comments
National Science Foundation, Grant 1338056