Photoactivatable Anthracenes

• DOI: 10.1021/jo5004482
• Publication Date: 2014-04-09T20:23:50Z
• Authors: Ek Raj Thapaliya; Burjor Captain; Françisco M. Raymo
• Keywords: Maleimide; Chromophore; Nitrogen atom

Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors yields ranging 32 to 63%. They differ the nature group on nitrogen atom and substituents platform. In all instances, introduction a bridge across positions 9 10 skeleton isolates electronically its peripheral phenylene rings suppresses characteristic fluorescence. The with 4-(dimethylamino)phenyl undergo retro-cycloaddition upon ultraviolet illumination quantum 0.001 0.01. This structural transformation restores aromatic character central ring oligoacene chromophore activates emission fluorescence 0.07 0.85. Thus, this particular choice building blocks for construction photoresponsive compounds can translate into viable operating principles activation and, ultimately, lead realization valuable photoactivatable fluorophores imaging applications.