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Titolo:
AXIALLY CHIRAL CATENANES AND PI-ELECTRON-DEFICIENT RECEPTORS
Autore:
ASAKAWA M; ASHTON PR; BOYD SE; BROWN CL; MENZER S; PASINI D; STODDART JF; TOLLEY MS; WHITE AJP; WILLIAMS DJ; WYATT PG;
Indirizzi:
UNIV BIRMINGHAM,SCH CHEM,POB 363 BIRMINGHAM B15 2TT W MIDLANDS ENGLAND UNIV BIRMINGHAM,SCH CHEM BIRMINGHAM B15 2TT W MIDLANDS ENGLAND UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,CHEM CRYSTALLOGLAB LONDON SW7 2AY ENGLAND GLAXO WELLCOME RES & DEV LTD,MED RES CTR STEVENAGE SG1 2NY HERTS ENGLAND
Titolo Testata:
Chemistry
fascicolo: 3, volume: 3, anno: 1997,
pagine: 463 - 481
SICI:
0947-6539(1997)3:3<463:ACCAPR>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIASTEREOSELECTIVE MOLECULAR RECOGNITION; ENANTIOSELECTIVE RECOGNITION; TRANSLATIONAL ISOMERISM; SYNTHETIC RECEPTOR; SOLID-STATE; SUPRAMOLECULAR CHEMISTRY; ORGANIC STRUCTURES; METAL-COMPLEXES; NOBEL LECTURE; HYDROGEN-BOND;
Keywords:
CATENANES; CHIRALITY; ENANTIO-SELECTION; RECEPTORS; SELF-ASSEMBLY;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
87
Recensione:
Indirizzi per estratti:
Citazione:
M. Asakawa et al., "AXIALLY CHIRAL CATENANES AND PI-ELECTRON-DEFICIENT RECEPTORS", Chemistry, 3(3), 1997, pp. 463-481

Abstract

The design of a new class of chiral [2]catenanes is reported. The self-assembly of [2]catenanes comprising one or two 3,3'-bitolyl spacers in the pi-electron-deficient component, and bis-p-phenylene-34-crown-10 (BPP34C10) as the pi-electron-rich component, is described. The X-ray crystal structures, together with solution-state dynamic H-1 NMR spectroscopic studies, show that the degree of order characterizing the molecular structures is substantially different from that of the ''parent'' [2]-catenane, comprising cyclobis(paraquat-p-phenylene) and BPP34C10. When appropriately substituted in their ortho positions, bitolyl compounds can support axial chirality: the self-assembly of axially chiral [2]catenanes, comprising one or two 3,3'-disubstituted-2,2'-dihydroxy-1,1'-binaphthyl spacers, has been achieved in good yields, showing that the introduction of the bulky, axially chiral spacer and the consequent distortion of the cavity of the pi-electron-deficient component still permits good molecular recognition between the components leading to efficient catenane production. X-ray crystallography suggests that this recognition is driven by hydrogen bonding and pi-pi stackinginteractions between the complementary subunits. The hydroxyl groups on the chiral spacer were further functionalized as benzoyl esters in a [2]catenane as well as in the tetracationic cyclophanes; that is, chemistry can be done on these catenanes. The chiral tetracationic cyclophanes exhibit good enantiomeric differentiation toward the D- and L-enantiomers of aromatic amino acids in water and their N-acetylated derivatives in organic solvents.

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Documento generato il 18/01/20 alle ore 13:11:30