Dendron rodcoils: Synthesis of novel organic hybrid structures

Eugene R. Zubarev, Samuel I Stupp

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

Convergent and divergent syntheses of novel organic hybrid structures termed dendron rodcoils (DRC) containing dendritic, rodlike, and coillike segments are described. The aryl ester dendron masked with 32 trifluoromethyl groups is prepared via a convergent approach using 5-(tert-butyldimethylsiloxy)-isophthalic acid as the monomer unit. The activation of the focal point of the dendron allows for successful coupling between the dendron and the diblock rodcoil molecules synthesized separately. In another example, the dendritic block is grown via divergent strategy from the terminus of rodcoil using 3,5-bis(tert-butyldimethylsiloxy)benzoic acid as an AB2 monomer. A combination of catalyzed esterification reactions and silyl deprotection chemistry proved to be a very efficient method for construction of these nanosized structures with unusual molecular architecture. Both synthetic strategies allowed for the preparation of DRCs with nearly monodisperse dendritic blocks as demonstrated by NMR, MALDI-TOF, and GPC measurements.

Original languageEnglish
Pages (from-to)5762-5773
Number of pages12
JournalJournal of the American Chemical Society
Volume124
Issue number20
DOIs
Publication statusPublished - May 22 2002

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Synthetic Chemistry Techniques
Monomers
Benzoic acid
Esterification
Esters
Chemical activation
Nuclear magnetic resonance
Molecules
Benzoic Acid
Acids
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
dendron

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Dendron rodcoils : Synthesis of novel organic hybrid structures. / Zubarev, Eugene R.; Stupp, Samuel I.

In: Journal of the American Chemical Society, Vol. 124, No. 20, 22.05.2002, p. 5762-5773.

Research output: Contribution to journalArticle

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