Linquats: Synthesis, Characterization, and Properties of Linear Extended Diquats. Issue 34 (13th July 2016)

• Record Type: Journal Article
• Authors: Čížková, Martina; Pospíšil, Lubomír; Klepetářová, Blanka; Koval, Dušan; Teplý, Filip
• Is Part Of: Chemistry. Volume 22:Issue 34(2016)
• Page Start: 12154
• Page End: 12159
• Publication Date: 2016-07-13
• Subjects: cycloaddition -- density functional calculations -- electrochemistry -- N-heterocyclic cations -- spectroscopy; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600819
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Electron‐deficient polycycles : Flexible synthetic entry to a family of small linear extended diquats (linquats) is reported. The physicochemical properties were studied by spectroscopic methods, X‐ray crystallography, electrochemistry, and DFT calculations.