Guanosine and fullerene derived de-aggregation of a new phthalocyanine-linked cytidine derivative

JL Sessler, J Jayawickramarajah, A Gouloumis, GD Pantos, T Torres, DM Guldi

Research output: Contribution to journalArticle

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Abstract

Electronic absorption and emission properties of a new cytidine tethered zinc phthalocyanine 2 were used to probe the aggregation and guanosine/C-60 derived de-aggregation of this nucleobase linked phthalocyanine. These experiments revealed that 2 aggregates even at low concentrations in a competitive solvent system (1.1 x 10(-6) M in 20% DCM/toluene). Nucleobase-metal coordination and slipped co-facial pi-stacking interactions are both important in aggregate formation. Guanosine 5, C-60 6, and a guanosine-C-60 chimera 4 were employed as potential aggregate disruptors. These experiments revealed that both guanosine and fullerene subunits are effective in disrupting the aggregate formed by 2. Such findings support the conclusion that base-pairing, pi-stacking, as well as nucleobase-metal coordination interactions play important roles in the de-aggregation of 2. (c) 2005 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2123-2131
Number of pages9
JournalTetrahedron
Volume62
Issue number9
Early online date21 Nov 2005
DOIs
Publication statusPublished - 27 Feb 2006

Fingerprint

Fullerenes
Cytidine
Guanosine
Agglomeration
Derivatives
Metals
Toluene
Base Pairing
Experiments
phthalocyanine

Keywords

  • phthalocyanine aggregation
  • phthalocyanine de-aggregation
  • fullerenes
  • nucleobases
  • non-covalent interactions
  • electronic spectra

Cite this

Guanosine and fullerene derived de-aggregation of a new phthalocyanine-linked cytidine derivative. / Sessler, JL; Jayawickramarajah, J; Gouloumis, A; Pantos, GD; Torres, T; Guldi, DM.

In: Tetrahedron, Vol. 62, No. 9, 27.02.2006, p. 2123-2131.

Research output: Contribution to journalArticle

Sessler, JL, Jayawickramarajah, J, Gouloumis, A, Pantos, GD, Torres, T & Guldi, DM 2006, 'Guanosine and fullerene derived de-aggregation of a new phthalocyanine-linked cytidine derivative', Tetrahedron, vol. 62, no. 9, pp. 2123-2131. https://doi.org/10.1016/j.tet.2005.05.110
Sessler, JL ; Jayawickramarajah, J ; Gouloumis, A ; Pantos, GD ; Torres, T ; Guldi, DM. / Guanosine and fullerene derived de-aggregation of a new phthalocyanine-linked cytidine derivative. In: Tetrahedron. 2006 ; Vol. 62, No. 9. pp. 2123-2131.
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AB - Electronic absorption and emission properties of a new cytidine tethered zinc phthalocyanine 2 were used to probe the aggregation and guanosine/C-60 derived de-aggregation of this nucleobase linked phthalocyanine. These experiments revealed that 2 aggregates even at low concentrations in a competitive solvent system (1.1 x 10(-6) M in 20% DCM/toluene). Nucleobase-metal coordination and slipped co-facial pi-stacking interactions are both important in aggregate formation. Guanosine 5, C-60 6, and a guanosine-C-60 chimera 4 were employed as potential aggregate disruptors. These experiments revealed that both guanosine and fullerene subunits are effective in disrupting the aggregate formed by 2. Such findings support the conclusion that base-pairing, pi-stacking, as well as nucleobase-metal coordination interactions play important roles in the de-aggregation of 2. (c) 2005 Elsevier Ltd. All rights reserved.

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