Hydroxycruciforms: Amine-responsive fluorophores

Psaras L. McGrier, Kyril M. Solntsev, Shaobin Miao, Laren M. Tolbert, Oscar R. Miranda, Vincent M. Rotello, Uwe H.F. Bunz

Research output: Contribution to journalArticle

72 Scopus citations

Abstract

The synthesis of three hydroxy-substituted cruciforms (XF, 1,4-bis(4′-hydroxystyryl)-2,5-bis(4″-methoxyphenylethynyl)benzene, 1,4-bis(4′-methoxystyryl)-2,5-bis(4″-hydroxyphenylethynyl)benzene, and 1,4-bis(4′-hydroxystyryl)-2,5-bis(4″-hydroxyphenylethynyl) benzene) starts with a Horner reaction followed by a Sonogashira coupling and subsequent deprotection. The three herein described XFs contain either two or four free phenolic hydroxyl groups. All three XFs were subjected to photometric UV/Vis titrations in a methanol/water mixture. The respective pK a values were obtained by data deconvolution. As the three XFs display a significant change in emission color upon photoinduced deprotonation, the XFs were taken up in different solvents and exposed to twelve amines. The amine-dependent change in emissivity of the tetrahydroxy XF is sufficiently distinct in the eight solvents that all of the inspected amines are discerned by a linear discriminant analysis. The tetrahydroxy XF in different solvents forms a sensor array, the response of which is based on the excited-state proton transfer (ESPT) to amines and mediated by the choice of the battery of solvents that are utilized.

Original languageEnglish (US)
Pages (from-to)4503-4510
Number of pages8
JournalChemistry - A European Journal
Volume14
Issue number15
DOIs
StatePublished - May 19 2008
Externally publishedYes

Keywords

  • Alkynes
  • Amines
  • Fluorescence
  • Sensors
  • Solvatochromism

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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  • Cite this

    McGrier, P. L., Solntsev, K. M., Miao, S., Tolbert, L. M., Miranda, O. R., Rotello, V. M., & Bunz, U. H. F. (2008). Hydroxycruciforms: Amine-responsive fluorophores. Chemistry - A European Journal, 14(15), 4503-4510. https://doi.org/10.1002/chem.200800296