Control of stilbene conformation and fluorescence in self-assembled capsules
The extensively studied trans-stilbene molecule is known to give only weak fluorescence in solution and inside loosely-fitting synthetic capsules. However, trans-stilbene has been recently studied in the context of antibody interiors, where binding results in strong blue fluorescence. The present re...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2009-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.5.79 |
| _version_ | 1818913604744773632 |
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| author | Mark R. Ams Dariush Ajami Stephen L. Craig Jye-Shane Yang Julius Rebek Jr |
| author_facet | Mark R. Ams Dariush Ajami Stephen L. Craig Jye-Shane Yang Julius Rebek Jr |
| author_sort | Mark R. Ams |
| collection | DOAJ |
| description | The extensively studied trans-stilbene molecule is known to give only weak fluorescence in solution and inside loosely-fitting synthetic capsules. However, trans-stilbene has been recently studied in the context of antibody interiors, where binding results in strong blue fluorescence. The present research was undertaken to understand the spatial factors that influence stilbene fluorescence. trans-Stilbene was encapsulated in the snug, self-assembled complex 1.1 and exhibited fluorescence quenching due to the distortion of its ground-state geometry. When the complex is elongated by incorporating glycouril spacers, trans-stilbene is allowed to adapt a fully coplanar arrangement and fluorescence returns. |
| first_indexed | 2024-12-19T23:33:08Z |
| format | Article |
| id | doaj.art-53efa88dbcb443589570287f97134997 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T23:33:08Z |
| publishDate | 2009-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-53efa88dbcb443589570287f971349972022-12-21T20:01:41ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972009-12-01517910.3762/bjoc.5.791860-5397-5-79Control of stilbene conformation and fluorescence in self-assembled capsulesMark R. Ams0Dariush Ajami1Stephen L. Craig2Jye-Shane Yang3Julius Rebek Jr4The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, U.S., Tel: 858 784 2250; Fax: 858 784 2876The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, U.S., Tel: 858 784 2250; Fax: 858 784 2876Department of Chemistry, Duke University, Durham, NC, 27708-0346, U.S.Department of Chemistry, National Taiwan University, No. 1. Sec. 4, Roosevelt Road, Taipei, 10617, TaiwanThe Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, U.S., Tel: 858 784 2250; Fax: 858 784 2876The extensively studied trans-stilbene molecule is known to give only weak fluorescence in solution and inside loosely-fitting synthetic capsules. However, trans-stilbene has been recently studied in the context of antibody interiors, where binding results in strong blue fluorescence. The present research was undertaken to understand the spatial factors that influence stilbene fluorescence. trans-Stilbene was encapsulated in the snug, self-assembled complex 1.1 and exhibited fluorescence quenching due to the distortion of its ground-state geometry. When the complex is elongated by incorporating glycouril spacers, trans-stilbene is allowed to adapt a fully coplanar arrangement and fluorescence returns.https://doi.org/10.3762/bjoc.5.79molecular twistingquenchingreversible encapsulationself-assemblystilbene fluorescence |
| spellingShingle | Mark R. Ams Dariush Ajami Stephen L. Craig Jye-Shane Yang Julius Rebek Jr Control of stilbene conformation and fluorescence in self-assembled capsules Beilstein Journal of Organic Chemistry molecular twisting quenching reversible encapsulation self-assembly stilbene fluorescence |
| title | Control of stilbene conformation and fluorescence in self-assembled capsules |
| title_full | Control of stilbene conformation and fluorescence in self-assembled capsules |
| title_fullStr | Control of stilbene conformation and fluorescence in self-assembled capsules |
| title_full_unstemmed | Control of stilbene conformation and fluorescence in self-assembled capsules |
| title_short | Control of stilbene conformation and fluorescence in self-assembled capsules |
| title_sort | control of stilbene conformation and fluorescence in self assembled capsules |
| topic | molecular twisting quenching reversible encapsulation self-assembly stilbene fluorescence |
| url | https://doi.org/10.3762/bjoc.5.79 |
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