{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,8,27]],"date-time":"2024-08-27T09:48:04Z","timestamp":1724752084473},"reference-count":52,"publisher":"Walter de Gruyter GmbH","issue":"11","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,11,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n\t\t\t\t<jats:p>The synthesis of two new inherently chiral calix[4]arenes (ICCs, <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold>), 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 (<jats:italic>S<\/jats:italic>)-Pirkle\u2019s alcohol unequivocally showed that the host-guest interactions occur in the chiral pocket comprehending the calix-OCP <jats:italic>exo<\/jats:italic> cavities and the carbazole moieties.<\/jats:p>","DOI":"10.1515\/pac-2014-0707","type":"journal-article","created":{"date-parts":[[2014,10,13]],"date-time":"2014-10-13T17:00:38Z","timestamp":1413219638000},"page":"1819-1828","source":"Crossref","is-referenced-by-count":4,"title":["Inherently chiral calix[4]arenes with planar chirality: two new entries to the family"],"prefix":"10.1515","volume":"86","author":[{"given":"Jos\u00e9 V.","family":"Prata","sequence":"first","affiliation":[]},{"given":"Patr\u00edcia D.","family":"Barata","sequence":"additional","affiliation":[]},{"given":"Gennaro","family":"Pescitelli","sequence":"additional","affiliation":[]}],"member":"374","reference":[{"key":"ref11","article-title":"an introduction in nded The of Chemistry","author":"Calixarenes","year":"2008","journal-title":"Supramolecular Chemistry Royal Society"},{"key":"ref91","doi-asserted-by":"crossref","first-page":"2511","DOI":"10.1021\/jo952054a","author":"Kanamathareddy","year":"1996","journal-title":"Org Chem"},{"key":"ref431","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1007\/BF00708972","volume":"19","author":"B\u00f6hmer","year":"1994","journal-title":"Inclusion Phenom Mol Recognit Chem"},{"key":"ref01","article-title":"Academic Dordrecht","author":"Asfari","year":"2001"},{"key":"ref381","first-page":"4527","author":"Gutsche","year":"1982","journal-title":"Org Chem"},{"key":"ref541","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1002\/hlca.201200471","author":"Testa","year":"2013","journal-title":"Helv Chim Acta"},{"key":"ref161","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1016\/j.tetasy.2014.02.012","volume":"25","author":"Prata","year":"2014","journal-title":"Tetrahedron"},{"key":"ref551","article-title":"Under the here reported conditions using trimethylbenzene as the void volume marker the separation \u03b1 and the resolution factors were calculated \u03b1 andRs and forrac \u03b1 andRs","volume":"17","author":"Forrac"},{"key":"ref31","doi-asserted-by":"crossref","first-page":"599","DOI":"10.1016\/0040-4020(94)00919-L","author":"Arduini","year":"1995","journal-title":"Tetrahedron"},{"key":"ref141","article-title":"New","volume":"28","author":"Cort","year":"1198","journal-title":"J Chem"},{"key":"ref241","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1002\/hlca.201200471","author":"Testa","year":"2013","journal-title":"Helv Chim Acta"},{"key":"ref331","doi-asserted-by":"crossref","first-page":"599","DOI":"10.1016\/0040-4020(94)00919-L","author":"Arduini","year":"1995","journal-title":"Tetrahedron"},{"key":"ref41","doi-asserted-by":"crossref","first-page":"8654","DOI":"10.1021\/jo9706990","author":"Pinkhassik","year":"1997","journal-title":"Org Chem"},{"key":"ref151","first-page":"39","year":"2010","journal-title":"Szumna Chem Soc Rev"},{"key":"ref411","doi-asserted-by":"crossref","first-page":"429","DOI":"10.3390\/ijms12010429","volume":"12","author":"Li","year":"2011","journal-title":"Int J Mol Sci"},{"key":"ref111","doi-asserted-by":"crossref","first-page":"429","DOI":"10.3390\/ijms12010429","volume":"12","author":"Li","year":"2011","journal-title":"Int J Mol Sci"},{"key":"ref291","article-title":"Since the four structures considered for each compound do not represent a true conformational ensemble calculated spectra were simply averaged and not weighted on the basis of relative energies","volume":"28"},{"key":"ref351","first-page":"62","article-title":"in Action College","author":"Casnati","year":"2000","journal-title":"Imperial"},{"key":"ref51","first-page":"62","article-title":"in Action College","author":"Casnati","year":"2000","journal-title":"Imperial"},{"key":"ref251","article-title":"Under the here reported conditions using trimethylbenzene as the void volume marker the separation \u03b1 and the resolution factors were calculated \u03b1 andRs and forrac \u03b1 andRs","volume":"17","author":"Forrac"},{"key":"ref471","first-page":"6602","author":"Prata","year":"2013","journal-title":"Tetrahedron Lett"},{"key":"ref501","first-page":"1","article-title":"Conformational searches ( Monte Carlo method MMFF force field ) were first performed on pS ) configurations of which were followed by geometry optimizations semi - empirical model ) of the lowest - energy conformers ; 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