2,2′:6′,2″‐Terpyridines Functionalized with Thienyl Substituents: Synthesis and Applications

Abstract

This review deals with the synthesis and applications of 2,2 0 :6 0 ,2 00 -terpyridines which are functionalized with thiophene ring, directly linked to the terpyridine core or via a spacer. Two main methodologies were used, ring closure of diketo-derivatives and cross coupling reactions. The obtained compounds find applications in various fields especially in material sciences such as solar cells or macromolecular sciences. Scheme 4. Synthesis of thienyl-containing quaterpyridine. Scheme 5 456

Anion Influence of Emission Properties and DFT Calculations of Diprotonated and Triprotonated Terpyridines

“…In diprotonated 1H , the protonation of two peripheral pyridine nitrogens was confirmed and dihedral angles N−C‐C−N of this compound are 4.0° and 5.8°. It is known that free terpy have a trans‐trans configuration . The distances of the intramolecular hydrogen bonds to the adjacent N atom were 1.967 and 2.017 Å (middle of Figure ).…”

“…It has been established that 2,2’:6’,2’’‐terpyridine has low quantum yield fluorescence and significant emission can be achieved after specific modification of the terpyridine, especially by introducing substituent at the 4’‐position . Huang et al.…”

Synthesis of new 4′-(N-alkylpyrrol-2-yl)-2,2′: 6′,2″-terpyridines via N-alkylation of a pyrrole moiety

“…This article describes the preparation of new alkyl-functionalized terpyridines through the N-alkylation of a pyrrole moiety attached to the terpyridine scaffold. This methodology was selected owing to the fact that terpyridines containing five-membered heterocycles are easily prepared [8,9] and the pyrrole ring can be easily modified at the N-atom [10].…”

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

“…While the number of publications concerning applications or investigations of inorganic–organic hybrid structures has increased enormously, comparably few fluorescent 4′-functionalized 2,2′:6′,2″-terpyridine derivatives have been reported [8]. It has been established that 2,2′:6′,2″-terpyridine has low quantum yield fluorescence [9] and significant emission can be achieved after specific modifications of the terpyridine core motif, especially by introducing conjugated moieties at the 4′-position [10–12]. In this context, the synthesis of tailored terpyridine derivatives with appropriate electron-donor/acceptor moieties may allow for a further improvement of their spectroscopic and electrochemical properties.…”