Synthesis of Ring-Fused Pyridinium Salts by Intramolecular Nucleophilic Aromatic Substitution Reaction and Their Optoelectronic Properties

Yuki Asanuma; Hiroshi Eguchi; Hiroki Nishiyama; Ikuyoshi Tomita; Shinsuke Inagi

doi:10.1021/acs.orglett.7b00590

Synthesis of Ring-Fused Pyridinium Salts by Intramolecular Nucleophilic Aromatic Substitution Reaction and Their Optoelectronic Properties

Org Lett. 2017 Apr 7;19(7):1824-1827. doi: 10.1021/acs.orglett.7b00590. Epub 2017 Mar 29.

Authors

Yuki Asanuma¹, Hiroshi Eguchi¹, Hiroki Nishiyama², Ikuyoshi Tomita², Shinsuke Inagi²

Affiliations

¹ Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology , 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan.
² Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology , 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8502, Japan.

PMID: 28355080
DOI: 10.1021/acs.orglett.7b00590

Abstract

The synthesis of nitrogen cation-doped polycyclic aromatic hydrocarbons (PAHs) having a variety of counteranions is reported via the trimethylsilyl (TMS)-promoted intramolecular aromatic nucleophilic substitution (S_NAr) reaction of fluoroarenes and pyridine groups. The electrochemical properties and optical properties of the obtained nitrogen cation-doped PAHs were studied in detail, clarifying that they have low-lying LUMO levels and good emission properties derived from the incorporation of planar N-arylpyridinium moieties.

Publication types

Research Support, Non-U.S. Gov't