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

65 Citations (Scopus)

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

Fingerprint

Fluorophores
Amines
Benzene
Deprotonation
Proton transfer
Sensor arrays
Discriminant analysis
Deconvolution
Titration
Excited states
Hydroxyl Radical
Methanol
Color
Water

Keywords

  • Alkynes
  • Amines
  • Fluorescence
  • Sensors
  • Solvatochromism

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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

Hydroxycruciforms : Amine-responsive fluorophores. / McGrier, Psaras L.; Solntsev, Kyril M.; Miao, Shaobin; Tolbert, Laren M.; Miranda, Oscar R.; Rotello, Vincent M.; Bunz, Uwe H.F.

In: Chemistry - A European Journal, Vol. 14, No. 15, 19.05.2008, p. 4503-4510.

Research output: Contribution to journalArticle

McGrier, PL, Solntsev, KM, Miao, S, Tolbert, LM, Miranda, OR, Rotello, VM & Bunz, UHF 2008, 'Hydroxycruciforms: Amine-responsive fluorophores', Chemistry - A European Journal, vol. 14, no. 15, pp. 4503-4510. https://doi.org/10.1002/chem.200800296
McGrier PL, Solntsev KM, Miao S, Tolbert LM, Miranda OR, Rotello VM et al. Hydroxycruciforms: Amine-responsive fluorophores. Chemistry - A European Journal. 2008 May 19;14(15):4503-4510. https://doi.org/10.1002/chem.200800296
McGrier, Psaras L. ; Solntsev, Kyril M. ; Miao, Shaobin ; Tolbert, Laren M. ; Miranda, Oscar R. ; Rotello, Vincent M. ; Bunz, Uwe H.F. / Hydroxycruciforms : Amine-responsive fluorophores. In: Chemistry - A European Journal. 2008 ; Vol. 14, No. 15. pp. 4503-4510.
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