{"title":"反式-α,α,α′,α′-四苯基-9,10-二氢-9,10-四氮杂蒽-11,12-二甲醇及其四(对氯苯基)衍生物:用于提纯芳香族 C8H10 异构客体混合物的屋顶形主化合物","authors":"Benita Barton, Ulrich Senekal, Eric C. Hosten","doi":"10.1007/s10847-021-01102-5","DOIUrl":null,"url":null,"abstract":"<div><p>Roof-shaped host compounds <i>trans</i>-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol <b>H3</b> and <i>trans</i>-α,α,α′,α′-tetra(<i>p</i>-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol <b>H6</b> were assessed for their host potential and selectivity behaviour when presented with single or mixed guest solvents comprising <i>o</i>-xylene, <i>m</i>-xylene, <i>p</i>-xylene and ethylbenzene (<i>o</i>-Xy, <i>m</i>-Xy, <i>p</i>-Xy and EB). <b>H3</b> included each solvent with 3:1 host:guest ratios, while the ratios preferred by <b>H6</b> were more varied (4:3, 1:1 and 3:2). More importantly, the selectivity behaviour of these two host compounds was observed to be entirely different: <b>H3</b> possessed only a very modest preference for <i>o</i>-Xy (37.9–68.2%) when recrystallized from various equimolar binary, ternary and quaternary guest mixtures, while <b>H6</b> was considerably more selective, preferring <i>m</i>-Xy (the least favoured guest of <b>H3</b>) with selectivities ranging from 57.7 to 91.4% in analogous conditions. The latter result was obtained in <i>o</i>-Xy/<i>m</i>-Xy mixtures and demonstrates that <b>H6</b> may be employed as a purification tool for mixtures of these two xylenes via host–guest chemistry protocols. A single crystal diffraction experiment on 3(<b>H3</b>)·<i>o</i>-Xy (containing the preferred guest of <b>H3</b>) revealed that the guest was retained in the host crystal by means of a singular (host)<i>m</i>-Ar–H···π(guest) interaction that measured 2.73 Å (148°) as well as numerous other host···guest interactions involving only the aromatic protons of the free host phenyl groups and the guest methyl protons or aromatic carbons and protons (2.20–2.54 Å, 121–125°). Thermal analyses explained the preference of <b>H3</b> for <i>o</i>-Xy, while these were less informative for the complexes of <b>H6</b>.\n</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"102 1-2","pages":"77 - 87"},"PeriodicalIF":2.3000,"publicationDate":"2021-09-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-021-01102-5.pdf","citationCount":"0","resultStr":"{\"title\":\"trans-α,α,α′,α′-Tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol and its tetra(p-chlorophenyl) derivative: roof-shaped host compounds for the purification of aromatic C8H10 isomeric guest mixtures\",\"authors\":\"Benita Barton, Ulrich Senekal, Eric C. Hosten\",\"doi\":\"10.1007/s10847-021-01102-5\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Roof-shaped host compounds <i>trans</i>-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol <b>H3</b> and <i>trans</i>-α,α,α′,α′-tetra(<i>p</i>-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol <b>H6</b> were assessed for their host potential and selectivity behaviour when presented with single or mixed guest solvents comprising <i>o</i>-xylene, <i>m</i>-xylene, <i>p</i>-xylene and ethylbenzene (<i>o</i>-Xy, <i>m</i>-Xy, <i>p</i>-Xy and EB). <b>H3</b> included each solvent with 3:1 host:guest ratios, while the ratios preferred by <b>H6</b> were more varied (4:3, 1:1 and 3:2). More importantly, the selectivity behaviour of these two host compounds was observed to be entirely different: <b>H3</b> possessed only a very modest preference for <i>o</i>-Xy (37.9–68.2%) when recrystallized from various equimolar binary, ternary and quaternary guest mixtures, while <b>H6</b> was considerably more selective, preferring <i>m</i>-Xy (the least favoured guest of <b>H3</b>) with selectivities ranging from 57.7 to 91.4% in analogous conditions. The latter result was obtained in <i>o</i>-Xy/<i>m</i>-Xy mixtures and demonstrates that <b>H6</b> may be employed as a purification tool for mixtures of these two xylenes via host–guest chemistry protocols. A single crystal diffraction experiment on 3(<b>H3</b>)·<i>o</i>-Xy (containing the preferred guest of <b>H3</b>) revealed that the guest was retained in the host crystal by means of a singular (host)<i>m</i>-Ar–H···π(guest) interaction that measured 2.73 Å (148°) as well as numerous other host···guest interactions involving only the aromatic protons of the free host phenyl groups and the guest methyl protons or aromatic carbons and protons (2.20–2.54 Å, 121–125°). Thermal analyses explained the preference of <b>H3</b> for <i>o</i>-Xy, while these were less informative for the complexes of <b>H6</b>.\\n</p></div>\",\"PeriodicalId\":638,\"journal\":{\"name\":\"Journal of Inclusion Phenomena and Macrocyclic Chemistry\",\"volume\":\"102 1-2\",\"pages\":\"77 - 87\"},\"PeriodicalIF\":2.3000,\"publicationDate\":\"2021-09-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://link.springer.com/content/pdf/10.1007/s10847-021-01102-5.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Inclusion Phenomena and Macrocyclic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10847-021-01102-5\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Agricultural and Biological Sciences\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-021-01102-5","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Agricultural and Biological Sciences","Score":null,"Total":0}
trans-α,α,α′,α′-Tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol and its tetra(p-chlorophenyl) derivative: roof-shaped host compounds for the purification of aromatic C8H10 isomeric guest mixtures
Roof-shaped host compounds trans-α,α,α′,α′-tetraphenyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol H3 and trans-α,α,α′,α′-tetra(p-chlorophenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol H6 were assessed for their host potential and selectivity behaviour when presented with single or mixed guest solvents comprising o-xylene, m-xylene, p-xylene and ethylbenzene (o-Xy, m-Xy, p-Xy and EB). H3 included each solvent with 3:1 host:guest ratios, while the ratios preferred by H6 were more varied (4:3, 1:1 and 3:2). More importantly, the selectivity behaviour of these two host compounds was observed to be entirely different: H3 possessed only a very modest preference for o-Xy (37.9–68.2%) when recrystallized from various equimolar binary, ternary and quaternary guest mixtures, while H6 was considerably more selective, preferring m-Xy (the least favoured guest of H3) with selectivities ranging from 57.7 to 91.4% in analogous conditions. The latter result was obtained in o-Xy/m-Xy mixtures and demonstrates that H6 may be employed as a purification tool for mixtures of these two xylenes via host–guest chemistry protocols. A single crystal diffraction experiment on 3(H3)·o-Xy (containing the preferred guest of H3) revealed that the guest was retained in the host crystal by means of a singular (host)m-Ar–H···π(guest) interaction that measured 2.73 Å (148°) as well as numerous other host···guest interactions involving only the aromatic protons of the free host phenyl groups and the guest methyl protons or aromatic carbons and protons (2.20–2.54 Å, 121–125°). Thermal analyses explained the preference of H3 for o-Xy, while these were less informative for the complexes of H6.
期刊介绍:
The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites.
The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.