Covalent nano-clip and nano-box compounds based on free base porphyrins

Autor: Placido Mineo, Daniele Vitalini, Emilio Scamporrino
Rok vydání: 2011
Předmět:
Zdroj: Tetrahedron (Oxf., Print) 67 (2011): 3705–3713. doi:10.1016/j.tet.2011.03.072
info:cnr-pdr/source/autori:E. Scamporrino, P. Mineo, D. Vitalini/titolo:Covalent nano-clip and nano-box compounds based on free base porphyrins/doi:10.1016%2Fj.tet.2011.03.072/rivista:Tetrahedron (Oxf., Print)/anno:2011/pagina_da:3705/pagina_a:3713/intervallo_pagine:3705–3713/volume:67
ISSN: 0040-4020
DOI: 10.1016/j.tet.2011.03.072
Popis: Novel nano-clip and nano-box compounds were obtained by reaction between dibromomethane and 5,15-di[p-(9-methoxytriethylenenoxy)phenyl]-10,20-di[p-hydroxyphenyl]porphyrin. The molecular architecture varies from a co-facial (nano-clip) to a four wall-box (nano-box) structure. The products were characterized by 1H NMR and UV–vis spectroscopy and MALDI-TOF mass spectrometric analysis. The UV–vis spectra of the nano-clip showed a modification of the characteristic porphyrin soret and Q bands, with respect to the monomer and cyclic tetramer, as a probable consequence of a hybrid orbital deformation (HOD) phenomenon involving the two porphyrin π rings forced to a closer co-facial spatial arrangement. The spatial distance between the two co-facial porphyrin units, and therefore the molecular cavity size, can be modified inducing an electrostatic repulsion by means of a reversible protonation of the pyrrolic cores. The 1H NMR spectra of the nano-box showed a strong high-field shift of some aromatic and ether protons present in the upper and lower rim of the molecular box.
Databáze: OpenAIRE
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