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Synthesis and Complexation Properties of an Oligooxaethylene‐Spacered Porphyrin Dimer – Toward the Construction of a New Switchable Porphyrin Array
Author(s) -
Monti Donato,
Venanzi Mariano,
Mancini Giovanna,
Marotti Federica,
La Monica Laura,
Boschi Tristano
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199908)1999:8<1901::aid-ejoc1901>3.0.co;2-r
Subject(s) - supramolecular chemistry , chemistry , porphyrin , dimer , yield (engineering) , proton nmr , supramolecular assembly , fluorescence , stereochemistry , combinatorial chemistry , crystallography , photochemistry , organic chemistry , crystal structure , materials science , physics , quantum mechanics , metallurgy
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. 1 H‐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 (CD 3 CN/CDCl 3 , 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.