Synlett 2018; 29(19): 2509-2514
DOI: 10.1055/s-0037-1610224
cluster
© Georg Thieme Verlag Stuttgart · New York

Fluorofluorescent Perylene Bisimides

Kosuke Yoshinaga
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA   Email: [email protected]
,
Timothy M. Swager*
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, MA 02139, USA   Email: [email protected]
› Author Affiliations
Financial support from the Air Force Office of Scientific Research is greatly appreciated. K.Y. thanks Funai Overseas Scholarship for financial support.
Further Information

Publication History

Received: 09 June 2018

Accepted after revision: 05 July 2018

Publication Date:
31 July 2018 (online)


Published as part of the Cluster Synthesis of Materials

Abstract

Perfluorinated liquids can exhibit immiscibility with organic solvents and water, and provide orthogonal opportunities in chemistry. Examples of emissive dyes that display only fluorous phase solubility are limited, despite the many potential applications. Perylene bisimides are among the most versatile dyes and are known for their outstanding stability and high quantum yields. Herein, we report the synthesis of two new “fluorofluorescent” perylene bisimide dyes, designed to be soluble in the fluorous phases. These two dyes possess unique photophysical properties, including dramatic increases in fluorescence quantum yields when treated with Brønsted acids as well as aggregation in the fluorous phase.

Supporting Information

 
  • References and Notes

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