Self-Assembly of a Functional Oligo(Aniline)-Based Amphiphile into Helical Conductive Nanowires

OA Bell, GL Wu, Johannes Haataja, F Brommel, N Fey, AM Seddon, RL Harniman, RM Richardson, O Ikkala, Xi Zhang, CFJ Faul

Research output: Contribution to journalArticleScientificpeer-review

43 Citations (Scopus)

Abstract

A tetra(aniline)-based cationic amphiphile, TANI-NHC(O)C5H10N(CH3)3(+)Br(-) (TANI-PTAB) was synthesized, and its emeraldine base (EB) state was found to self-assemble into nanowires in aqueous solution. The observed self-assembly is described by an isodesmic model, as shown by temperature-dependent UV/Vis investigations. Linear dichroism (LD) studies, combined with computational modeling using time-dependent density functional theory (TD-DFT), suggests that TANI-PTAB molecules are ordered in an anti-parallel arrangement within nanowires, with the long axis of TANI-PTAB arranged perpendicular to the nanowire long axis. Addition of either S- or R- camphorsulfonic acid (CSA) to TANI-PTAB converted TANI to the emeraldine salt (ES), which retained the ability to form nanowires. Acid doping of TANI-PTAB had a profound effect on the nanowire morphology, as the CSA counter-ions' chirality translated into helical twisting of the nanowires, as observed by circular dichroism (CD). Finally, the electrical conductivity of CSA-doped helical nanowire thin films processed from aqueous solution was 2.7 mS cm(-1). The conductivity, control over self-assembled 1D structure and water-solubility demonstrate these materials' promise as processable and addressable functional materials for molecular electronics, redox-controlled materials and sensing.
Original languageEnglish
Pages (from-to)14288-14294
JournalJournal of the American Chemical Society
Volume137
Issue number45
DOIs
Publication statusPublished - 2015
MoE publication typeA1 Journal article-refereed

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