Journal article

Amine-Substituted Diazocine Derivatives - Synthesis, Structure, and Photophysical Properties

Mark A Gregory, Bolong Zhang, Andrew J Tilley, Tamika Scheerlinck, Jonathan M White, Wallace WH Wong

HELVETICA CHIMICA ACTA | WILEY-V C H VERLAG GMBH | Published : 2018

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.

Grants

Awarded by Australian Research Council


Awarded by ARC Centre of Excellence in Exciton Science


Funding Acknowledgements

This work was made possible by support from the Australian Research Council through a Future Fellowship (WWHW, FT130100500) and the ARC Centre of Excellence in Exciton Science (CE170100026). W. W. H. W. and B. Z. were further supported by Australian Renewable Energy Agency which funds the project grants within the Australian Centre for Advanced Photovoltaics (ACAP). Responsibility for the views, information or advice expressed herein is not accepted by the Australian Government.