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Linquats: Synthesis, Characterization, and Properties of Linear Extended Diquats
Author(s) -
Čížková Martina,
Pospíšil Lubomír,
Klepetářová Blanka,
Koval Dušan,
Teplý Filip
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600819
Subject(s) - intramolecular force , cycloaddition , electrochemistry , chemistry , redox , combinatorial chemistry , alkyne , electron transfer , computational chemistry , nanotechnology , stereochemistry , materials science , photochemistry , organic chemistry , electrode , catalysis
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.