An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change
The hydrophobic/hydrophilic ratio in a molecule largely affects its assembled properties in aqueous media. In this study, we synthesized a new bicyclic compound which could dynamically change its hydrophobic/hydrophilic ratio by chemical stimulus. The bicyclic compound consisted of amphiphilic pilla...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2018-07-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.167 |
| _version_ | 1818916417818329088 |
|---|---|
| author | Tomoki Ogoshi Tomohiro Akutsu Tada-aki Yamagishi |
| author_facet | Tomoki Ogoshi Tomohiro Akutsu Tada-aki Yamagishi |
| author_sort | Tomoki Ogoshi |
| collection | DOAJ |
| description | The hydrophobic/hydrophilic ratio in a molecule largely affects its assembled properties in aqueous media. In this study, we synthesized a new bicyclic compound which could dynamically change its hydrophobic/hydrophilic ratio by chemical stimulus. The bicyclic compound consisted of amphiphilic pillar[5]arene and hydrophobic alkyl chain rings, and formed a self-inclusion structure in aqueous media, which was assigned as a pseudo[1]catenane structure. The hydrophobic chain ring was hidden inside the pillar[5]arene cavity in the pseudo[1]catenane structure, thus the bicyclic compound was soluble in water at 20 °C with a clouding point at 24 °C. The pseudo[1]catenane was converted to the de-threaded structure upon addition of the neutral guest 1,4-dicyanobutane, which displaced the alkyl chain ring from the inside to the outside of the cavity. The hydrophobic alkyl chain ring was now exposed to the aqueous media, causing aggregation of the hydrophobic alkyl chain rings, which induced insolubilization of the bicyclic compound in aqueous media at 20 °C and a decrease in its clouding point. |
| first_indexed | 2024-12-20T00:17:51Z |
| format | Article |
| id | doaj.art-55f90c869656469f9d66a0890a886b94 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T00:17:51Z |
| publishDate | 2018-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-55f90c869656469f9d66a0890a886b942022-12-21T20:00:16ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-07-011411937194310.3762/bjoc.14.1671860-5397-14-167An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point changeTomoki Ogoshi0Tomohiro Akutsu1Tada-aki Yamagishi2Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, JapanGraduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, JapanGraduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, JapanThe hydrophobic/hydrophilic ratio in a molecule largely affects its assembled properties in aqueous media. In this study, we synthesized a new bicyclic compound which could dynamically change its hydrophobic/hydrophilic ratio by chemical stimulus. The bicyclic compound consisted of amphiphilic pillar[5]arene and hydrophobic alkyl chain rings, and formed a self-inclusion structure in aqueous media, which was assigned as a pseudo[1]catenane structure. The hydrophobic chain ring was hidden inside the pillar[5]arene cavity in the pseudo[1]catenane structure, thus the bicyclic compound was soluble in water at 20 °C with a clouding point at 24 °C. The pseudo[1]catenane was converted to the de-threaded structure upon addition of the neutral guest 1,4-dicyanobutane, which displaced the alkyl chain ring from the inside to the outside of the cavity. The hydrophobic alkyl chain ring was now exposed to the aqueous media, causing aggregation of the hydrophobic alkyl chain rings, which induced insolubilization of the bicyclic compound in aqueous media at 20 °C and a decrease in its clouding point.https://doi.org/10.3762/bjoc.14.167amphiphilic moleculeshost–guest complexeslower critical solution temperaturepillar[n]arenespseudo[1]catenane |
| spellingShingle | Tomoki Ogoshi Tomohiro Akutsu Tada-aki Yamagishi An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change Beilstein Journal of Organic Chemistry amphiphilic molecules host–guest complexes lower critical solution temperature pillar[n]arenes pseudo[1]catenane |
| title | An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change |
| title_full | An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change |
| title_fullStr | An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change |
| title_full_unstemmed | An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change |
| title_short | An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change |
| title_sort | amphiphilic pseudo 1 catenane neutral guest induced clouding point change |
| topic | amphiphilic molecules host–guest complexes lower critical solution temperature pillar[n]arenes pseudo[1]catenane |
| url | https://doi.org/10.3762/bjoc.14.167 |
| work_keys_str_mv | AT tomokiogoshi anamphiphilicpseudo1catenaneneutralguestinducedcloudingpointchange AT tomohiroakutsu anamphiphilicpseudo1catenaneneutralguestinducedcloudingpointchange AT tadaakiyamagishi anamphiphilicpseudo1catenaneneutralguestinducedcloudingpointchange AT tomokiogoshi amphiphilicpseudo1catenaneneutralguestinducedcloudingpointchange AT tomohiroakutsu amphiphilicpseudo1catenaneneutralguestinducedcloudingpointchange AT tadaakiyamagishi amphiphilicpseudo1catenaneneutralguestinducedcloudingpointchange |