Sterically shielded tetrazoles for a fluorogenic photoclick reaction: tuning cycloaddition rate and product fluorescence?

Organic & Biomolecular Chemistry Pub Date: 2018-07-04 DOI: 10.1039/C8OB01404C

Abstract

A panel of sterically shielded tetrazoles with different N-aryl groups were synthesized and subsequently evaluated in the photoinduced tetrazole–alkene cycloaddition reaction. It was found that increase in the HOMO energy of the corresponding nitrile imines leads to a faster cycloaddition reaction along with a red shift in the fluorescence emission of the pyrazoline cycloadduct.

Graphical abstract: Sterically shielded tetrazoles for a fluorogenic photoclick reaction: tuning cycloaddition rate and product fluorescence
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