Bulky melamine-based Zn-porphyrin tweezer as a CD probe of molecular chirality (Articolo in rivista)

Type
Label
  • Bulky melamine-based Zn-porphyrin tweezer as a CD probe of molecular chirality (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/chir.21001 (literal)
Alternative label
  • A. G. Petrovic, G. Vantomme, Y. L. Negrón-Abril, E. Lubian, G. Saielli, I. Menegazzo, R. Cordero, G. Proni, K. Nakanishi, T. Carofiglio, N. Berova (2011)
    Bulky melamine-based Zn-porphyrin tweezer as a CD probe of molecular chirality
    in Chirality (N.Y., N.Y. Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • A. G. Petrovic, G. Vantomme, Y. L. Negrón-Abril, E. Lubian, G. Saielli, I. Menegazzo, R. Cordero, G. Proni, K. Nakanishi, T. Carofiglio, N. Berova (literal)
Pagina inizio
  • 808 (literal)
Pagina fine
  • 819 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://onlinelibrary.wiley.com/doi/10.1002/chir.21001/abstract (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 23 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Department of Life Sciences, New York Institute of Technology (NYIT), New York, New York Department of Chemistry, Columbia University, New York, New York Dipartimento di Scienze Chimiche, Universita` di Padova, Padova, Italy Istituto per la Tecnologia delle Membrane del CNR, Sezine di Padova, Science Department, John Jay College, New York, New York (literal)
Titolo
  • Bulky melamine-based Zn-porphyrin tweezer as a CD probe of molecular chirality (literal)
Abstract
  • The transfer of chirality from a guest molecule to an achiral host is the subject of significant interest especially when, upon chiral induction, the chiroptical response of the host/guest complex can effectively report the absolute configuration (AC) of the guest. For more than a decade, dimeric metalloporphyrin hosts (tweezers) have been successfully applied as chirality probes for determination of the AC for a wide variety of chiral synthetic compounds and natural products. The objective of this study is to investigate the utility of a new class of melamine-bridged Zn-porphyrin tweezers as sensitive AC reporters. A combined approach based on an experimental CD analysis and a theoretical prediction of the prevailing interporphyrin helicity demonstrates that these tweezers display favorable properties for chiral recognition. Herein, we discuss the application of the melamine-bridged tweezer to the chiral recognition of a diverse set of chiral guests, such as 1,2-diamines, a-amino-esters and amides, secondary alcohols, and 1,2-amino-alcohols. The bulky periphery and the presence of a rigid porphyrin linkage lead, in some cases, to a more enhanced CD sensitivity than that reported earlier with other tweezers. (literal)
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