Linquats: Synthesis, Characterization, and Properties of Linear Extended Diquats

0464357 - ÚOCHB 2017 RIV DE eng J - Journal Article
Čížková, Martina - Pospíšil, Lubomír - Klepetářová, Blanka - Koval, Dušan - Teplý, Filip
Linquats: Synthesis, Characterization, and Properties of Linear Extended Diquats.
Chemistry - A European Journal. Roč. 22, č. 34 (2016), s. 12154-12159. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR GA13-19213S; GA ČR GA13-32974S
Institutional support: RVO:61388963 ; RVO:61388955
Keywords : cycloaddition * density functional calculations * electrochemistry * N-heterocyclic cations * spectroscopy
Subject RIV: CC - Organic Chemistry; CG - Electrochemistry (UFCH-W)
Impact factor: 5.317, year: 2016

We report an innovative synthetic route to linear extended diquats (linquats). Our approach is short and efficient and features a highly modular reaction sequence based on two-fold quaternization followed by the key intramolecular [2+ 2+ 2] alkyne cycloaddition. The physico-chemical properties of four new linquats were characterized by spectroscopic methods, X-ray crystallography, and electrochemistry complemented by information obtained from DFT calculations. Electron deficient N-heteroaromatic cations with linear extended diquat motif with high electron affinities have been recently recognized as attractive n-type semiconductors for chemical and biological sensing. Their advantageous redox properties such as very fast reversible electron transfers make the title compounds interesting for applications.
Permanent Link: http://hdl.handle.net/11104/0263266