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Titolo:
Modular synthesis of pi-acceptor cyclophanes derived from 1,4,5,8-naphthalenetetracarboxylic diimide and 1,5-dinitronaphthalene
Autore:
Chen, GY; Lean, JT; Alcala, M; Mallouk, TE;
Indirizzi:
Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ University Pk PA USA 16802 m, University Pk, PA 16802 USA
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 9, volume: 66, anno: 2001,
pagine: 3027 - 3034
SICI:
0022-3263(20010504)66:9<3027:MSOPCD>2.0.ZU;2-J
Fonte:
ISI
Lingua:
ENG
Soggetto:
CHIRAL MOLECULAR RECOGNITION; PHASE PEPTIDE-SYNTHESIS; MERRIFIELD-RESINS; BINDING; RECEPTOR; HOST; CYCLOBIS(PARAQUAT-PARA-PHENYLENE); ELECTROCHEMISTRY; BENZYLVIOLOGEN; COMPLEXES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
44
Recensione:
Indirizzi per estratti:
Indirizzo: Mallouk, TE Penn State Univ, Dept Chem, University Pk, PA 16802 USA Penn State Univ University Pk PA USA 16802 y Pk, PA 16802 USA
Citazione:
G.Y. Chen et al., "Modular synthesis of pi-acceptor cyclophanes derived from 1,4,5,8-naphthalenetetracarboxylic diimide and 1,5-dinitronaphthalene", J ORG CHEM, 66(9), 2001, pp. 3027-3034

Abstract

Three neutral cyclophanes were synthesized, and their association with indole, an aromatic pi -donor, was studied. The cyclophanes were designed to contain a rigid, hydrophobic binding cavity with 1,4,5,8-naphthalenetetracarboxylic diimide or 1,5-dinitronaphthalene as the pi -acceptor. Two of the cyclophanes also contain a (S)-(valine-leucine-alanine) tripeptide unit to provide chiral hydrogen bonding interactions with guest molecules. Despite the fact that these cyclophanes contain a hydrophobic binding cavity of appropriate dimensions, their association with indole is very weak. In the caseof cyclophanes derived from 1,5-dinitronaphthalene, steric inter actions force the nitro groups out of the plane of the naphthalene ring, diminishingtheir effectiveness as pi -acceptors. A simple UV-visible titrimetric method, using N,N,N',N'-tetramethyl-1,4-phenylenediamine (TMPD) as a pi -donor,was used to rank the pi -acceptor strength of these and other aromatic units. These titrations show that 1,4,5,8-naphthalenetetracarboxylic diimide and 1,5-dinitronaphthalene derivatives are weaker pi -acceptors than viologens, which make good;pi -acceptor cyclophanes. Methyl viologen is in turn a weaker pi -acceptor than anthaquinone disulfonate. suggesting that the latter may serve as a useful building block for pi -accepting cyclophane hosts.

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Documento generato il 12/08/20 alle ore 20:23:48