2012
DOI: 10.1002/chem.201200371
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Absolute Stereochemical Determination of Chiral Carboxylates Using an Achiral Molecular Tweezer

Abstract: A new type of molecular tweezer (1) has been synthesized for the direct determination of the absolute configuration of chiral carboxylates without analyte derivatization. Upon the addition of diamine and anionic guests, 1 exhibited shifts in its absorption spectrum with clear isosbestic points. The continuous variation method indicated that both the diamine and anionic guests form 1:1 host-guest complexes with 1 with very high binding affinity. When Boc-L-Ala (BLA) as a form of tetrabutylammonium salt was adde… Show more

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Cited by 40 publications
(25 citation statements)
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“…In the case of the peripherally substituted AB 3 ‐Pcs 19 , the circular dichroism is more pronounced than in the case of the non‐peripherally substituted AB 3 ‐Pc 15 . This phenomenon has already been described by Yoon and colleagues in 2012 . In this case, dimeric porphyrins of the clamshell type with large staggering angles θ showed a stronger cotton effect than the porphyrins with small staggering angles θ.…”
Section: Resultssupporting
confidence: 72%
“…In the case of the peripherally substituted AB 3 ‐Pcs 19 , the circular dichroism is more pronounced than in the case of the non‐peripherally substituted AB 3 ‐Pc 15 . This phenomenon has already been described by Yoon and colleagues in 2012 . In this case, dimeric porphyrins of the clamshell type with large staggering angles θ showed a stronger cotton effect than the porphyrins with small staggering angles θ.…”
Section: Resultssupporting
confidence: 72%
“…The general need for derivatization of substrates that do not afford two amino groups has been overcome with the development of increasingly Lewis acidic metalloporphyrins and tweezer designs exhibiting a short or rigid linker. [73][74][75] Borhan and coworkers introduced fluorinated porphyrin tweezer 42 for the direct determination of the absolute configuration of amino alcohols, epoxy alcohols and diols (Fig. 19).…”
Section: Porphyrinsmentioning
confidence: 99%
“…moieties. Consequently, molecular tweezers can act as receptors for a wide variety of substrates ranging from carbon materials [3,4], anions [5,6], organic [7] and inorganic cations [8] and neutral organic guests [9]. The general use and applications of molecular tweezers in the complexation of a variety of substrates has been reviewed in several accounts [10,11,12].…”
Section: Insert Figurementioning
confidence: 99%