US EPA

1469025 

Journal Article 

Core-substituted naphthalene bisimides: new fluorophors with tunable emission wavelength for FRET studies 

Würthner, F; Ahmed, S; Thalacker, C; Debaerdemaeker, T 

2002 

Yes 

Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 

8 

20 

4742-4750 

English 

12561114 

10.1002/1521-3765(20021018)8:20<4742::AID-CHEM4742>3.0.CO;2-L 

WOS:000178873100016 

http://://WOS:000178873100016
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Highly colored and photoluminescent naphthalene bisimide dyes have been synthesized from 2,6-dichloronaphthalene bisanhydride 1 by means of a stepwise nucleophilic displacement of the two chlorine atoms by alkoxides and/or alkyl amines. The alkoxy-substituted derivatives are yellow dyes with green emission and low photoluminescence quantum yields, whereas the amine-substituted derivatives exhibit a color range from red to blue with strong photoluminescence up to 76%. Structure-property relationships for this class of two-dimensional chromophores were evaluated based on a single-crystal X-ray analysis for dye 5a, the observed solvatochromism, and quantum-chemical calculations. Owing to the simple tuning of the absorption properties over the whole visible range by the respective substituents, the pronounced brilliancy, and the intense photoluminescence, this class of dyes is considered to be highly suited for numerous applications such as fluorescent labeling of biomacromolecules and light-harvesting in supramolecular assemblies. As an important step towards such applications efficient FRET (fluorescence resonance energy transfer) has been demonstrated for a covalently tethered bichromophoric compound that contains a red and a blue naphthalene bisimide dye. 

chromophores; dyes/pigments; fluorescence; FRET (fluorescence resonance energy transfer); nucleophilic substitution