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- Publisher Website: 10.1002/1521-3765(20000616)6:12<2262::AID-CHEM2262>3.0.CO;2-G
- Scopus: eid_2-s2.0-0034674234
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Article: Self-complementary [2]catenanes and their related [3]catenanes
Title | Self-complementary [2]catenanes and their related [3]catenanes |
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Authors | |
Keywords | Catenanes Crystal engineering Molecular recognition Supramolecular chemistry Template synthesis |
Issue Date | 2000 |
Citation | Chemistry - A European Journal, 2000, v. 6, n. 12, p. 2262-2273 How to Cite? |
Abstract | Three [3]catenanes with cavities large enough to accommodate aromatic guests have been designed and synthesized (yields = 5-20%) by means of kinetically controlled self-assembly processes. The X-ray structural analysis of one of three [3]catenanes confirmed the presence of a rectangular cavity (dimensions = 7 ×11 Å) lined by π-electron-rich recognition sites and hydro-gen-bond acceptor groups. In spite of their apparently ideal recognition features, none of these [3]catenanes bind guests incorporating a π-electron-deficient bipyridinium unit. However, the template-directed syntheses of the [3]catenanes also produce, in yields of 2-23%, [2]catenanes incorporating a l,5-dioxynaphtho[38]crown-10 inter-locked with a bipyridinium-based tetracationic cyclophane. The X-ray structural analyses of two of these [2]catenanes revealed that a combination of [π⋯π] and [C-H⋯π] interactions is responsible for the formation of supramolecular homodimers in the solid state. 1H NMR spectroscopic investigations of the four [2]catenanes demonstrated that supramolecular homodimers are also formed (Ka= 17-31M-1, T= 185 K) in (CD3)2CO solutions. Dynamic 1H NMR spectroscopy revealed that the 1,5-dioxynaphtho[38]crown-10 and tetracationic cyclophane components in the four [2]catenanes and in the three [3]catenanes circumrotate (ΔGC‡ = 9-14 kcal mol-1) through each other's cavity in (CD3)2CO. Similarly, the 1,5-dioxynaphthalene and the bipyridinium ring systems rotate (ΔGc‡ =10-14 kcalmol-1) about their [O⋯O] and [N ⋯ N] axes, respectively, in solution. |
Persistent Identifier | http://hdl.handle.net/10722/332477 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Cabezon, Beatriz | - |
dc.contributor.author | Cao, Jianguo | - |
dc.contributor.author | Raymo, Françisco M. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.contributor.author | White, Andrew J.P. | - |
dc.contributor.author | Williams, David J. | - |
dc.date.accessioned | 2023-10-06T05:11:49Z | - |
dc.date.available | 2023-10-06T05:11:49Z | - |
dc.date.issued | 2000 | - |
dc.identifier.citation | Chemistry - A European Journal, 2000, v. 6, n. 12, p. 2262-2273 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332477 | - |
dc.description.abstract | Three [3]catenanes with cavities large enough to accommodate aromatic guests have been designed and synthesized (yields = 5-20%) by means of kinetically controlled self-assembly processes. The X-ray structural analysis of one of three [3]catenanes confirmed the presence of a rectangular cavity (dimensions = 7 ×11 Å) lined by π-electron-rich recognition sites and hydro-gen-bond acceptor groups. In spite of their apparently ideal recognition features, none of these [3]catenanes bind guests incorporating a π-electron-deficient bipyridinium unit. However, the template-directed syntheses of the [3]catenanes also produce, in yields of 2-23%, [2]catenanes incorporating a l,5-dioxynaphtho[38]crown-10 inter-locked with a bipyridinium-based tetracationic cyclophane. The X-ray structural analyses of two of these [2]catenanes revealed that a combination of [π⋯π] and [C-H⋯π] interactions is responsible for the formation of supramolecular homodimers in the solid state. 1H NMR spectroscopic investigations of the four [2]catenanes demonstrated that supramolecular homodimers are also formed (Ka= 17-31M-1, T= 185 K) in (CD3)2CO solutions. Dynamic 1H NMR spectroscopy revealed that the 1,5-dioxynaphtho[38]crown-10 and tetracationic cyclophane components in the four [2]catenanes and in the three [3]catenanes circumrotate (ΔGC‡ = 9-14 kcal mol-1) through each other's cavity in (CD3)2CO. Similarly, the 1,5-dioxynaphthalene and the bipyridinium ring systems rotate (ΔGc‡ =10-14 kcalmol-1) about their [O⋯O] and [N ⋯ N] axes, respectively, in solution. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | Catenanes | - |
dc.subject | Crystal engineering | - |
dc.subject | Molecular recognition | - |
dc.subject | Supramolecular chemistry | - |
dc.subject | Template synthesis | - |
dc.title | Self-complementary [2]catenanes and their related [3]catenanes | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/1521-3765(20000616)6:12<2262::AID-CHEM2262>3.0.CO;2-G | - |
dc.identifier.scopus | eid_2-s2.0-0034674234 | - |
dc.identifier.volume | 6 | - |
dc.identifier.issue | 12 | - |
dc.identifier.spage | 2262 | - |
dc.identifier.epage | 2273 | - |
dc.identifier.isi | WOS:000087852600023 | - |