Photoswitchable fluorescent dyads incorporating bodipy and [1,3]oxazine components

Erhan Deniz, Shuvasree Ray, Massimiliano Tomasulo, Stefania Impellizzeri, Salvatore Sortino, Francisco Raymo

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

We designed and synthesized three compounds incorporating a BODIPY fluorophore and an oxazine photochrome within the same molecular skeleton and differing in the nature of the linker bridging the two functional components. The [1,3]oxazine ring of the photochrome opens in less than 6 ns upon laser excitation in two of the three fluorophore-photochrome dyads. This process generates a 3H-indolium cation with a quantum yield of 0.02-0.05. The photogenerated isomer has a lifetime of 1-3 μs and reverts to the original species with first-order kinetics. Both photochromic systems tolerate hundreds of switching cycles with no sign of degradation. The visible excitation of the dyads is accompanied by the characteristic fluorescence of the BODIPY component. However, the cationic fragment of their photogenerated isomers can accept an electron or energy from the excited fluorophore. As a result, the photoinduced transformation of the photochromic component within each dyad results in the effective quenching of the BODIPY emission. Indeed, the fluorescence of these photoswitchable compounds can be modulated on a microsecond time scale with excellent fatigue resistance under optical control. Thus, our operating principles and choice of functional components can ultimately lead to the development of valuable photoswitchable fluorescent probes for the super-resolution imaging of biological samples.

Original languageEnglish
Pages (from-to)11567-11575
Number of pages9
JournalJournal of Physical Chemistry A
Volume114
Issue number43
DOIs
StatePublished - Nov 4 2010

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Oxazines
Fluorophores
Isomers
Fluorescence
Laser excitation
isomers
Quantum yield
Fluorescent Dyes
fluorescence
optical control
Cations
Quenching
musculoskeletal system
Fatigue of materials
excitation
Imaging techniques
Degradation
Kinetics
Electrons
quenching

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Photoswitchable fluorescent dyads incorporating bodipy and [1,3]oxazine components. / Deniz, Erhan; Ray, Shuvasree; Tomasulo, Massimiliano; Impellizzeri, Stefania; Sortino, Salvatore; Raymo, Francisco.

In: Journal of Physical Chemistry A, Vol. 114, No. 43, 04.11.2010, p. 11567-11575.

Research output: Contribution to journalArticle

Deniz, E, Ray, S, Tomasulo, M, Impellizzeri, S, Sortino, S & Raymo, F 2010, 'Photoswitchable fluorescent dyads incorporating bodipy and [1,3]oxazine components', Journal of Physical Chemistry A, vol. 114, no. 43, pp. 11567-11575. https://doi.org/10.1021/jp107116d
Deniz, Erhan ; Ray, Shuvasree ; Tomasulo, Massimiliano ; Impellizzeri, Stefania ; Sortino, Salvatore ; Raymo, Francisco. / Photoswitchable fluorescent dyads incorporating bodipy and [1,3]oxazine components. In: Journal of Physical Chemistry A. 2010 ; Vol. 114, No. 43. pp. 11567-11575.
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