Direct synthesis of fluorescent 1,3a,6a-triazapentalene derivatives via click-cyclization-aromatization cascade reaction

Kosuke Namba; Ayumi Osawa; Shoji Ishizaka; Noboru Kitamura; Keiji Tanino

doi:10.1021/ja203917r

Direct synthesis of fluorescent 1,3a,6a-triazapentalene derivatives via click-cyclization-aromatization cascade reaction

J Am Chem Soc. 2011 Aug 3;133(30):11466-9. doi: 10.1021/ja203917r. Epub 2011 Jul 13.

Authors

Kosuke Namba¹, Ayumi Osawa, Shoji Ishizaka, Noboru Kitamura, Keiji Tanino

Affiliation

¹ Division of Chemistry, Graduate School of Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan. namba@mail.sci.hokudai.ac.jp

PMID: 21736311
DOI: 10.1021/ja203917r

Abstract

An efficient and versatile method was established for the preparation of 1,3a,6a-triazapentalenes. The 1,3a,6a-triazapentalene skeleton without an additional fused ring system was discovered to be a compact and highly fluorescent chromophore, which exhibited various interesting fluorescent properties such as a noteworthy correlation of luminescent wavelength with the Hammett σ(p) value and a strongly positive solvatofluorochromism.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Click Chemistry
Crystallography, X-Ray
Cyclization
Fluorescence*
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

1,3a,6a-triazapentalene
Bridged Bicyclo Compounds, Heterocyclic