Photoactivatable anthracenes

Ek Raj Thapaliya, Burjor Captain, Francisco Raymo

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

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

Original languageEnglish
Pages (from-to)3973-3981
Number of pages9
JournalJournal of Organic Chemistry
Volume79
Issue number9
DOIs
StatePublished - May 2 2014

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this