Synthesis and Complexation Properties of an Oligooxaethylene-Spacered Porphyrin Dimer – Toward the Construction of a New Switchable Porphyrin Array

Abstract

A new linear switchable diporphyrin array has been synthesized in good yield by a Williamson coupling of 5‐(4′‐hydroxyphenyl)‐10,15,20‐triphenylporphyrin with tetraethylene glycol ditosylate. 1H‐NMR binding studies reveal that the title receptor binds to Na+ and K+ salts to give a supramolecular complex with stability constants (K) of 30 and 160 M–1, respectively (CD3CN/CDCl3, 1:1). The formation of the host‐guest complexes promotes a change of the geometry of the system toward a topology in which the two tetrapyrrolic macrocycles tend to face together. UV/Vis and fluorescence spectroscopy give indications of the actual geometry of the assembly. The system reported represents an important step toward the construction of a supramolecular model of relevant biological systems.

Podand‐Based Dimeric Chromium(III)–Salen Complex for Asymmetric Henry Reaction: Cooperative Catalysis Promoted by Complexation of Alkali Metal Ions

“…Furthermore, Nonlinear data fitting14 delivered the association constant K a =79±12 for binding a guest K + . This result is in accordance with the reported value 3a. The Job plot analysis gave a 1:1 host/guest ratio (see the Supporting Information, Figure S3).…”

Synthesis and Studies of New Fluorescein‐Porphyrin Dyads: A Theoretical and Experimental Approach

“…of benzaldehyde 6 and 4 equiv. of pyrrole 5 (Scheme compounds, 8 was obtained with a 7% yield, in agreement with the literature ,. It should be noted 16% yield was recently obtained by a novel method…”

Construction and complexation studies of some self-assembled diporphyrin receptors

“…The synthesis of the porphyrin sub-units 1H 2 and 1Zn was accomplished by following a modification [10] of earlier reported methodologies [11], that entailed the acid catalysed aerobic cyclisation reaction from pyrrole, benzaldehyde, and pcarboxybenzaldehyde precursors in the appropriate molar ratio. Porphyrin sub-unit 1Zn was achieved quantitatively, by standard zinc acetate/methanol procedures, from 1H 2 [5].…”