Heterocyclic Chromophore Amphiphiles and their Supramolecular Polymerization |
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Authors: | Dr. Luka Đorđević Dr. Hiroaki Sai Dr. Yang Yang Dr. Nicholas A. Sather Dr. Liam C. Palmer Prof. Dr. Samuel I. Stupp |
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Affiliation: | 1. Center for Bio-Inspired Energy Science, Northwestern University, Evanston, IL, 60208 USA;2. Simpson Querrey Institute for BioNanotechnology, Northwestern University, Chicago, IL, 60611 USA |
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Abstract: | Supramolecular polymerization of π-conjugated amphiphiles in water is an attractive approach to create functional nanostructures. Here, we report on the synthesis, optoelectronic and electrochemical properties, aqueous supramolecular polymerization, and conductivity of polycyclic aromatic dicarboximide amphiphiles. The chemical structure of the model perylene monoimide amphiphile was modified with heterocycles, essentially substituting one fused benzene ring with thiophene, pyridine or pyrrole rings. All the heterocycle-containing monomers investigated underwent supramolecular polymerization in water. Large changes to the monomeric molecular dipole moments led to nanostructures with low electrical conductivity due to diminished interactions. Although the substitution of benzene with thiophene did not notably change the monomer dipole moment, it led to crystalline nanoribbons with 20-fold higher electrical conductivity, due to enhanced dispersion interactions as a result of the presence of sulfur atoms. |
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Keywords: | Chromophores Doping Nanostructures Self-Assembly Supramolecular Chemistry |
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