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Titolo:
MOLECULAR AND SUPRAMOLECULAR SYNTHESIS WITH DIBENZOFURAN-CONTAINING SYSTEMS
Autore:
ASAKAWA M; ASHTON PR; BROWN CL; FYFE MCT; MENZER S; PASINI D; SCHEUER C; SPENCER N; STODDART JF; WHITE AJP; WILLIAMS DJ;
Indirizzi:
UNIV BIRMINGHAM,SCH CHEM,POB 363 BIRMINGHAM B15 2TT W MIDLANDS ENGLAND UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM LONDON SW7 2AY ENGLAND
Titolo Testata:
Chemistry
fascicolo: 7, volume: 3, anno: 1997,
pagine: 1136 - 1150
SICI:
0947-6539(1997)3:7<1136:MASSWD>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
SOLID-STATE STRUCTURES; HYDROGEN-BONDING CONTROL; BETA-SHEET STRUCTURE; CRYSTAL-STRUCTURE; CONTAINING )2>CATENANE; NONCOVALENT SYNTHESIS; SELF-ORGANIZATION; ORGANIC-SYNTHESIS; CROWN-ETHER; AMINO-ACID;
Keywords:
CRYSTAL ENGINEERING; DIBENZOFURAN; MOLECULAR QUADRILATERALS; SUPRAMOLECULAR CHEMISTRY; TEMPLATE SYNTHESIS;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
157
Recensione:
Indirizzi per estratti:
Citazione:
M. Asakawa et al., "MOLECULAR AND SUPRAMOLECULAR SYNTHESIS WITH DIBENZOFURAN-CONTAINING SYSTEMS", Chemistry, 3(7), 1997, pp. 1136-1150

Abstract

The template-directed syntheses of two new tetracationic cyclophanes,cyclobis(paraquat-2.8-dibenzofuran) and cyclobis(paraquat-3.7-dibenzofuran), incorporating dibenzofuran subunits has been accomplished. Initially, the cyclophanes were self-assembled around a macrocyclic polyether template, bis-p-phenylene[34]crown-10 (BPP 34 C 10), to form catenanes: the mechanical bond order of the catenane formed determined therequisite ''amacrocyclic'' templates for synthesis of the free cyclophane. X-ray crystallography shows that both of the cyclophanes possessrectangular covalent frameworks. Furthermore, these cyclophanes form self-assembled tapes in the solid state, since the dibenzofuran moieties have a tendency to associate with each other through crossed pi-pi stacks. The dibenzofuran-containing catenanes also form two-dimensional supramolecular arrays in the solid state on account of extended pi-pi stacking interactions. In addition, the serendipitous discovery of aplerotopic tecton (consisting of a dibenzofuran nucleus covalently linked from the 2- and 8-positions by methylene groups to 4.4'-pyridylpyridinium (hydrogen bond acceptor) and protonated bipyridinium (hydrogen bond donor) units) has been made, The tecton dimerizes in the solid state to form a supramolecular macrocycle, since its complementary hydrogen bonding sites are oriented in a horseshoe-like fashion by the 2.8-disubstituted dibenzofuran unit, However, this superstructure is notretained in the 1:1 complex of the tecton with BPP 34 C 10: cocrystallization of the tecton with this crown ether opens the macrocyclic two-component supermolecule to afford a hydrogen-bonded pseudopolyrotaxane.

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Documento generato il 19/01/20 alle ore 20:16:46