Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives

Haishi Cao, Virginia Chang, Randy Hernandez, Michael D. Heagy

Research output: Contribution to journalArticle

108 Scopus citations

Abstract

A 3 × 14 matrix of substituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of dual fluorescence. Because of their unique photophysical properties, these dual fluorescent systems represent an exception to the widely studied TICT (Twisted Internal Charge Transfer) fluorescent dyes or tautomeric benzofluorescein class of two-color dyes. The matrix library was designed to investigate the effects of heterocycles, particularly π-excessive and π-deficient systems. Of the 42 compounds surveyed, five displayed well-resolved two-color emission in solvents as nonpolar as hexane. Based on the observed trends in fluorescence λmax and quantum yield, a new model is proposed that predicts LW and SW emission for these systems. In addition, this model provides potential design features for the synthesis of new dual fluorescent species.

Original languageEnglish (US)
Pages (from-to)4929-4934
Number of pages6
JournalJournal of Organic Chemistry
Volume70
Issue number13
DOIs
StatePublished - Jun 24 2005

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives'. Together they form a unique fingerprint.

  • Cite this