Porphyrin-containing glycodendrimers

Roberto Ballardini, Barbara Colonna, M. T. Gandolfi, Stacey A. Kalovidouris, Lukasz Orzel, Francisco Raymo, J. Fraser Stoddart

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Two dendrimers, incorporating tetrasubstituted porphyrin units as their cores and, in one case, four perbenzoylated and, in the other case, twelve peracetylated β-D-glucopyranosyl residues at their peripheries, have been synthesized in yields of 39 and 16%, respectively. The deprotection of these dendrimers was achieved quantitatively under Zemplén conditions. The protected and deprotected dendrimers were characterized by liquid secondary-ion or matrix-assisted laser desorption ionization time-of-flight mass spectrometry and by a combination of one- and two-dimensional 1H and 13C NMR spectroscopy. All the glycodendrimers were also characterized by absorption and emission spectroscopy, and lifetime measurements. The most relevant result is that both protected and deprotected dendrimers show two fluorescence lifetime values that are different from the porphyrin model compounds.

Original languageEnglish
Pages (from-to)288-294
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number2
StatePublished - Jan 1 2003

Fingerprint

Dendrimers
Porphyrins
dendrimers
porphyrins
life (durability)
Emission spectroscopy
Absorption spectroscopy
spectroscopy
Nuclear magnetic resonance spectroscopy
Ionization
Mass spectrometry
Desorption
absorption spectroscopy
mass spectroscopy
desorption
Fluorescence
Ions
ionization
fluorescence
nuclear magnetic resonance

Keywords

  • Carbohydrates
  • Convergent synthesis
  • Dendrimers
  • Luminescence
  • Porphyrins

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ballardini, R., Colonna, B., Gandolfi, M. T., Kalovidouris, S. A., Orzel, L., Raymo, F., & Stoddart, J. F. (2003). Porphyrin-containing glycodendrimers. European Journal of Organic Chemistry, (2), 288-294.

Porphyrin-containing glycodendrimers. / Ballardini, Roberto; Colonna, Barbara; Gandolfi, M. T.; Kalovidouris, Stacey A.; Orzel, Lukasz; Raymo, Francisco; Stoddart, J. Fraser.

In: European Journal of Organic Chemistry, No. 2, 01.01.2003, p. 288-294.

Research output: Contribution to journalArticle

Ballardini, R, Colonna, B, Gandolfi, MT, Kalovidouris, SA, Orzel, L, Raymo, F & Stoddart, JF 2003, 'Porphyrin-containing glycodendrimers', European Journal of Organic Chemistry, no. 2, pp. 288-294.
Ballardini R, Colonna B, Gandolfi MT, Kalovidouris SA, Orzel L, Raymo F et al. Porphyrin-containing glycodendrimers. European Journal of Organic Chemistry. 2003 Jan 1;(2):288-294.
Ballardini, Roberto ; Colonna, Barbara ; Gandolfi, M. T. ; Kalovidouris, Stacey A. ; Orzel, Lukasz ; Raymo, Francisco ; Stoddart, J. Fraser. / Porphyrin-containing glycodendrimers. In: European Journal of Organic Chemistry. 2003 ; No. 2. pp. 288-294.
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