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Synfacts 2013; 9(1): 0038
DOI: 10.1055/s-0032-1317886
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Large Stokes Shift from Triazine–o-Phenol Dyes

Contributor(s):
Timothy M. Swager
,
Silvia V. Rocha
Rihn S, Retailleau P, De Nicola A, Ulrich G, Ziessel R * Université de Strasbourg and Laboratoire de Crystallochimie, Gif-sur-Yvette, France
Synthetic Routes to Fluorescent Dyes Exhibiting Large Stokes Shifts.

J. Org. Chem. 2012;
77: 8851-8863
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

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Key words

fluorescent dyes - triazine

Significance

Fluorescent dyes exhibiting large Stokes shifts are of great interest for a multitude of applications. The authors report a straight-forward synthesis of a series of phenol–triazine dyes that exhibit hydrogen bonding in the ground state and undergo excited state intramolecular proton transfer (ESIPT), leading to the observation of large Stokes shifts.


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Comment

An exception to the observation of a large Stokes shift is the perylene-substituted dye; in this case, the perylene is responsible for the emission observed and the energy transfer occurs from the keto form to the perylene moiety. Also noteworthy is the large range of absorption and emission maxima exhibited by the family of dyes in this report.


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