Inherently chiral calix[4]arenes with planar chirality: two new entries to the family

被引：4

作者：

Prata, Jose V. ^{[1
,2
]}

Barata, Patricia D. ^{[1
,2
]}

Pescitelli, Gennaro ^{[3
]}

机构：

[1] Inst Politecn Lisboa, Inst Super Engn Lisboa, Dept Engn Quim, Lab Quim Organ, P-1959007 Lisbon, Portugal

[2] Inst Politecn Lisboa, Inst Super Engn Lisboa, Ctr Invest Engn Quim & Biotecnol, P-1959007 Lisbon, Portugal

[3] Univ Pisa, Dipartimento Chim & Chim Ind, I-56124 Pisa, Italy

来源：

PURE AND APPLIED CHEMISTRY | 2014年 / 86卷 / 11期

关键词：

absolute configuration assignment; Calix[4]arenes; chiroptical properties; fluorescence; POC-2014; planar chirality; TDDFT calculations; CHIROPTICAL PROPERTIES; CALIXARENES; RECOGNITION; RESOLUTION;

D O I：

10.1515/pac-2014-0707

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of two new inherently chiral calix[4]arenes (ICCs, 1 and 2), endowed with electron-rich concave surfaces, has been achieved through the desymmetrization of a lower rim distal-bridged oxacyclophane (OCP) macrocycle. The new highly emissive ICCs were resolved by chiral HPLC, and the enantiomeric nature of the isolated antipodes proved by electronic circular dichroism (CD). Using time-dependent density functional calculations of CD spectra, their absolute configurations were established. NMR studies with (S)-Pirkle's alcohol unequivocally showed that the host-guest interactions occur in the chiral pocket comprehending the calix-OCP exo cavities and the carbazole moieties.

引用

页码：1819 / 1828

页数：10

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