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Synthesis and structure elucidation of large phosphorus macrocycles

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Tinant, Bernard [UCL] Delangle, Pascale Mulatier, Jean-Christophe Declercq, Jean-Paul [UCL] Dutasta, Jean-Pierre

The simple reaction between 1,omega-diamino derivatives and R-bis-(dimethylamino)-phosphane (R = CH3, C6H5), followed by an oxidation step led to the formation of the expected macrocyclic phosphorus compounds. By this way 17- to 27-membered macrocycles were easily obtained. During the synthesis, the formation of dimeric (40- and 52-membered rings) and trimeric (78-membered rings) macrocyclic species were obtained from 3 and 5 and fully characterized by NMR and mass spectrometry. The P(III) phosphorus species exchange in solution and the macrocycle/oligomers ratio is temperature and concentration dependent. The crystal structure analysis of macrocycles 1, 5, 7 and 8 show that voids are minimized in the solid so that the macrocyclic cavity is filled up with part of the molecule itself or with a guest molecule, when the size of the macrocycle does not allow molecular folding for self-filling the cavity.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2007
Language Anglais
Journal information "Journal of Inclusion Phenomena and Molecular Recognition in Chemistry" - Vol. 58, no. 1-2, p. 139-149 (2007)
Peer reviewed yes
Publisher Springer (Dordrecht)
issn 0923-0750
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords macrocyclic compounds ; oligomers ; phosphoramide ; phosphorus macrocycles ; supramolecular chemistry ; X-ray analysis
Links
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Bibliographic reference Tinant, Bernard ; Delangle, Pascale ; Mulatier, Jean-Christophe ; Declercq, Jean-Paul ; Dutasta, Jean-Pierre. Synthesis and structure elucidation of large phosphorus macrocycles. In: Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, Vol. 58, no. 1-2, p. 139-149 (2007)
Permanent URL http://hdl.handle.net/2078.1/37635