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.
A one-pot synthetic method was established for the preparation of 2,5-disubstituted-1,3a,6a-triazapentalenes. The fluorescence observation of the synthetic 2,5-disubstituted-1,3a,6a-triazapentalenes revealed that the introduction of a substituent at the C5 position allowed a substantial change in the fluorescence quantum yield with little effect on the fluorescence wavelength.
To expand the function of the fluorescent 1,3a,6a-triazapentalenes as labelling reagents, their fluorescence wavelength was extended to the red color region.
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