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Linquats: Synthesis, Characterization, and Properties of Linear Extended Diquats
Martina Čížková1, Lubomír Pospíšil1,2, Blanka Klepetářová1
1Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10, Prague 6, Czech Republic.
Abstract:
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.
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