Oligodeoxyfluorosides: strong sequence dependence of fluorescence emission

James N Wilson, Jianmin Gao, Eric T. Kool

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

We describe the properties of a series of oligomeric polyfluorophores assembled on the DNA backbone. The 11 oligomers (oligodeoxyfluorosides, ODFs), 4-7 monomers in length, were composed of only two fluorescent monomers and a spacer in varied sequences, and were designed to test how fluorescent nucleobases can interact electronically to yield complexity in fluorescence emission. The monomer fluorophores were deoxyribosides of pyrene and perylene, which emit light in violet and blue wavelengths, respectively. The experiments show that simple variation in sequence and spacing can dramatically change fluorescence, yielding emission maxima ranging from 380 to 557 nm and visible colors from violet to orange-red. Fluorescence lifetime data, excitation spectra, and absorption data point to a number of multi-fluorophore electronic interactions, including pyrene-pyrene and perylene-perylene excimers, pyrene-perylene exciplexes, as well as monomer dye emissions, contributing to the final spectral outcomes. Thus, two simple fluorophores can be readily combined to give emissions over much of the visible spectrum, all requiring only a single excitation. The results demonstrate that fluorescent nucleobases in oligomeric form can act cooperatively as electronic units, and that fluorophore sequence in such oligomers is as important as fluorophore composition in determining fluorescence properties.

Original languageEnglish
Pages (from-to)3427-3433
Number of pages7
JournalTetrahedron
Volume63
Issue number17
DOIs
StatePublished - Apr 23 2007
Externally publishedYes

Fingerprint

Perylene
Fluorophores
Fluorescence
Monomers
Oligomers
Coloring Agents
Color
Light
pyrene
DNA
Wavelength
Chemical analysis
Experiments

Keywords

  • Excimer
  • Exciplex
  • Perylene
  • Pyrene
  • Stokes shift

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Oligodeoxyfluorosides : strong sequence dependence of fluorescence emission. / Wilson, James N; Gao, Jianmin; Kool, Eric T.

In: Tetrahedron, Vol. 63, No. 17, 23.04.2007, p. 3427-3433.

Research output: Contribution to journalArticle

Wilson, James N ; Gao, Jianmin ; Kool, Eric T. / Oligodeoxyfluorosides : strong sequence dependence of fluorescence emission. In: Tetrahedron. 2007 ; Vol. 63, No. 17. pp. 3427-3433.
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