Amine‐Substituted Diazocine Derivatives – Synthesis, Structure, and Photophysical Properties. Issue 11 (8th November 2018)

• Record Type: Journal Article
• Authors: Gregory, Mark A.; Zhang, Bolong; Tilley, Andrew J.; Scheerlinck, Tamika; White, Jonathan M.; Wong, Wallace W. H.
• Is Part Of: Helvetica chimica acta. Volume 101:Issue 11(2018)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2018-11-08
• Subjects: Diazocines -- eight-membered rings -- saddle-shaped structures -- electrochemical reduction -- electrochemistry -- photophysics; Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201800146
• Languages: English
• ISSNs: 0018-019X

Abstract

Abstract: A series of amine‐substituted diazocines were synthesized in three steps from methyl 2‐aminobenzoate or methyl 3‐aminonaphtholate. The saddle‐shaped diazocine compounds showed similar interplane angle of 75° despite the different steric bulk of the amine substituents. In electrochemical experiments, these diazocines showed irreversible reduction most likely producing indolo[3, 2‐ b ]indoles rather than forming the 10‐electron planar aromatic species. The carbazole‐substituted naphthodiazocines showed the most interesting photophysical properties with evidence of transition from the saddle‐shaped ground state to a planar excited state geometry. Abstract :