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Bulky melamine‐based Zn‐porphyrin tweezer as a CD probe of molecular chirality
Author(s) -
Petrovic Ana G.,
Vantomme Ghislaine,
NegrónAbril Yashira L.,
Lubian Elisa,
Saielli Giacomo,
Menegazzo Ileana,
Cordero Roselynn,
Proni Gloria,
Nakanishi Koji,
Carofiglio Tommaso,
Berova Nina
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21001
Subject(s) - chirality (physics) , tweezers , molecular tweezers , chemistry , porphyrin , melamine , molecule , axial chirality , molecular recognition , stereochemistry , combinatorial chemistry , supramolecular chemistry , photochemistry , organic chemistry , enantioselective synthesis , catalysis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
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, α‐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. Chirality, 2011. © 2011 Wiley‐Liss, Inc.