D-π-A Structures based on [1,2,4]triazolo[c]quinazolines: multifunctional fluorescent molecules

Abstract

Triazolo[c]quinazolines provide a promising molecular platform for various pharmaceutical applications and materials sciences . Novel tricyclic fluorophores A were obtained from 2-aryl-[1,2,4]triazolo[1,5-c]quinazoline-5(6H)-ones through chlorodesoxygenation and subsequent Suzuki–Miyaura cross-coupling reactions . The synthetic approach to triazolo[c]quinazoline derivatives B‒D is based on the condensation of 4-hydrazino-2-(5-bromothiophen-2-yl)quinazoline with various aryl(hetaryl) aldehydes, followed by oxidative cyclization with bromine at room temperature , or condensation with orthoester and subsequent cross-coupling reactions with aminoarylboronic acids or their pinacol esters. Some compounds exhibited pronounced fluorescence (over 95%) both in solution and the solid state. Moreover, they displayed solvatochromic properties and AIE activity.

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References

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