Melt-induced fluorescent signature in a simple naphthalenediimide

Toby D. M. Bell; Sheshanath V. Bhosale; Craig M. Forsyth; David Hayne; Kenneth P. Ghiggino; James A. Hutchison; Chintan H. Jani; Steven J. Langford; Marcia A.-P. Lee; Clint P. Woodward

doi:10.1039/C0CC00865F

Melt-induced fluorescent signature in a simple naphthalenediimide†

Toby D. M. Bell,^ab Sheshanath V. Bhosale,^a Craig M. Forsyth,^a David Hayne,^b Kenneth P. Ghiggino,*^b James A. Hutchison,‡^b Chintan H. Jani,^a Steven J. Langford,*^a Marcia A.-P. Lee^a and Clint P. Woodward^a

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* Corresponding authors

^a School of Chemistry, Monash University, Clayton, Victoria, Australia
E-mail: steven.langford@sci.monash.edu.au
Fax: +61 3 9905 4597
Tel: +61 3 9905 4569

^b School of Chemistry, The University of Melbourne, Victoria, Australia
E-mail: ghiggino@unimelb.edu.au
Fax: +61 3 9347 5180
Tel: +61 3 8344 8939

Abstract

The synthesis and fluorescence properties of a naphthalenediimide ditosylate are presented. The fluorescence is highly solvent and morphology dependent with a dramatic change in fluorescence output occurring following melting from a crystalline form. This observation is attributed to thermal disruption of the crystal structure allowing the formation of emissive dimers within the amorphous melt.

Chemical Communications

Melt-induced fluorescent signature in a simple naphthalenediimide†

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Melt-induced fluorescent signature in a simple naphthalenediimide

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