Controlling Solubility and Modulating Peripheral Function in Dendrimer Encapsulated Dyes

Paul Furuta, Jean Frechet

Research output: Contribution to journalArticlepeer-review

67 Scopus citations

Abstract

The synthesis of large dendrons and dendrimers with site-isolated dyes at their core has been explored. The dyes selected for this work were coumarin 343 and pentathiophene, as energy transfer processes prevail when the two dyes are intimately mixed but each should behave independently of the other if site-isolation is achieved. Because the two dyes have very different functional characteristics, a protocol involving orthogonal protecting groups and allowing the use of a single family of electroactive dendrons for their encapsulation had to be developed. The synthetic protocol must balance the need to incorporate electroactive groups at the periphery of the dendrons with the requirement for high solubility and a size sufficient to fully encapsulate the central dye. Because of their poor solubility and tendency to crystallize, dendrons with uniform triarylamine substitution proved unsatisfactory leading to the development of new unsymmetrical dendrons with alternating branched alkyl groups and triarylamine moieties at their periphery. These dendrons, which show excellent solubility and no tendency to crystallize, were assembled into large dendrimers using a modular protocol with the light emitting dye at their core. It is expected that the large size of the dendritic shell will provide effective site-isolation for the encapsulated central dyes enabling them to exhibit their intrinsic emission properties with minimal energy transfer between neighboring core fluorophores when processed in bulk thin films.

Original languageEnglish (US)
Pages (from-to)13173-13181
Number of pages9
JournalJournal of the American Chemical Society
Volume125
Issue number43
DOIs
StatePublished - Oct 29 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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