Elsevier

Tetrahedron Letters

Volume 48, Issue 19, 7 May 2007, Pages 3471-3474
Tetrahedron Letters

Modifications of DCDHF single molecule fluorophores to impart water solubility

https://doi.org/10.1016/j.tetlet.2007.03.026Get rights and content

Abstract

A series of dicyanomethylenedihydrofuran (DCDHF) fluorophores with different hydrophilic groups were synthesized and their photophysical properties and water solubilities were measured. Significant water solubility was achieved without compromising desirable photophysical properties, permitting applications of these fluorophores in biological systems.

Graphical abstract

A dicarboxylic acid substituted DCDHF dye (left two vials) and a sulfonic acid substituted DCDHF dye (right two vials) in liquid water (l) and ice (s) under UV irradiation.

  1. Download : Download full-size image

Section snippets

Acknowledgments

Support from DOE (DG-FG02-04ER63777), NIH (1P20HG003638-01) and the Ohio Board of Regents is acknowledged.

References and notes (16)

  • P.J. Schuck et al.

    Chem. Phys.

    (2005)
  • H. Wang et al.

    Tetrahedron

    (2007)
  • U. Gubler et al.

    Adv. Mater.

    (2002)
  • O. Ostroverkhova et al.

    ChemPhysChem

    (2003)
  • W. You et al.

    Adv. Mater.

    (2004)
  • O. Ostroverkhova et al.

    Appl. Phys. Lett.

    (2003)
  • K.A. Willets et al.

    J. Phys. Chem. B

    (2004)
  • K.A. Willets et al.

    Acc. Chem. Res.

    (2005)
There are more references available in the full text version of this article.

Cited by (23)

  • Selective detection of human serum albumin by near infrared emissive fluorophores: Insights into structure-property relationship

    2019, Journal of Photochemistry and Photobiology A: Chemistry
    Citation Excerpt :

    Several far-red and NIR emitting fluorophores have been reported in literature. Although each fluorophore has some distinct merits over another, some of the common demerits of NIR fluorophores are, poor aqueous solubility, aggregation-caused quenching, marginal output signal, and insufficient detection limit [26–28]. Above all the most frequently encountered demerit is lack of selectivity of the fluorophores for HSA [11,20].

  • Amino sulfonic acids, peptidosulfonamides and other related compounds

    2018, Tetrahedron
    Citation Excerpt :

    In the above examples, the ASA residues were introduced into the molecular probes either as parts of the linkers or as the water-solubilizing side chains. In fact, many other works described design of dyes or sensors with improved aqueous solubility by introducing fragments of ASA.556–568 An alternative use of the ASA was demonstrated for the cysteic acid residue in the molecule of photoreactive α-amino acid 834 (Fig. 66).569

  • Modification of D-π-A chromophore for the improvement of solubility in water

    2015, Materials Letters
    Citation Excerpt :

    As more and more D-π-A molecules are designed and prepared, the application of this kind of functional molecules in single molecule level has attracted the researchers' attention. Recently, the application of D-π-A molecules in viscosity dependent fluorescence, strong solvatochromism, significant ground state dipole moment, second harmonic generation imaging, molecular probe and fluorescence imaging has been reported as a new direction [6–10]. Compared with the traditional application of D-π-A molecules in optoelectronic devices, the largest difference is the requirements in water solubility.

  • Fluorescent penetration enhancers for transdermal applications

    2012, Journal of Controlled Release
    Citation Excerpt :

    However, in spite of the fact that DCDHF exhibited potency at a low concentration, it is limited by its poor water solubility. This structure, which has been shown to be readily derivatized [32,33], may be improved by adding a water-soluble group such as sulfonic acid (e.g. fluorophore 21 in [33], shown in Figure S5). Third, in spite of the fact that SRG and SRB have similar chemical structures, SRG is a significant FPE, while SRB is not.

  • D-π-A solvatochromic charge transfer dyes containing a 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran acceptor

    2010, Dyes and Pigments
    Citation Excerpt :

    9-Formyljulolidine 3 was synthesized according to the literature [21]. Dye 1–2 were prepared by the literature procedure [22–24]. The redox potentials were measured by cyclic voltammetry on an VersaSTAT3 model.

View all citing articles on Scopus
View full text