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- Publisher Website: 10.1002/chem.200305725
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- PMID: 15146527
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Article: Molecular shuttles based on tetrathiafulvalene units and 1,5-dioxynaphthalene ring systems
Title | Molecular shuttles based on tetrathiafulvalene units and 1,5-dioxynaphthalene ring systems |
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Authors | |
Keywords | Molecular shuttles Nanotechnology NMR spectroscopy Rotaxanes Self-assembly Template synthesis |
Issue Date | 2004 |
Citation | Chemistry - A European Journal, 2004, v. 10, n. 10, p. 2555-2564 How to Cite? |
Abstract | Six different degenerate [2]rotaxanes were synthesized and characterized. The rotaxanes contained either two tetrathiafulvalene (TTF) units or two 1,5-dioxynaphthalene (DNP) ring systems, both of which serve as recognition sites for a cyclobis(paraquat-p-phenylene) (CBPQT4+) ring. Three different spacer units were incorporated into the dumbbell components of the [2]rotaxanes between the recognition sites. They include a polyether chain, a terphenyl unit, and a diphenyl ether linker, all of which were investigated in order to probe the effect of the spacers on the rate of the shuttling process. Data from dynamic 1H NMR spectroscopy revealed a relatively small difference in the ΔG‡ values for the shuttling process in the [2]rotaxanes containing the three different spacers, in contrast to a large difference between the TTF-containing rotaxanes (18 kcalmol-1) and the DNP-containing rotaxanes (15 kcalmol-1). This 3 kcal mol -1 difference is predominantly a result of a ground-state effect, reflecting the much stronger binding of TTF units to the CBPQT4+ ring in comparison with DNP ring systems. An examination of the enthalpic (ΔH‡) and entropic (ΔS‡) components for the shuttling process in the DNP-containing rotaxanes revealed significant differences between the three spacers, a property which could be important in designing new molecules for incorporation into molecular electronic and nanoelectromechanical (NEMs) devices. |
Persistent Identifier | http://hdl.handle.net/10722/332647 |
ISSN | 2021 Impact Factor: 5.020 2020 SCImago Journal Rankings: 1.687 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Kang, Seogshin | - |
dc.contributor.author | Vignon, Scott A. | - |
dc.contributor.author | Tseng, Hsian Rong | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:13:11Z | - |
dc.date.available | 2023-10-06T05:13:11Z | - |
dc.date.issued | 2004 | - |
dc.identifier.citation | Chemistry - A European Journal, 2004, v. 10, n. 10, p. 2555-2564 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332647 | - |
dc.description.abstract | Six different degenerate [2]rotaxanes were synthesized and characterized. The rotaxanes contained either two tetrathiafulvalene (TTF) units or two 1,5-dioxynaphthalene (DNP) ring systems, both of which serve as recognition sites for a cyclobis(paraquat-p-phenylene) (CBPQT4+) ring. Three different spacer units were incorporated into the dumbbell components of the [2]rotaxanes between the recognition sites. They include a polyether chain, a terphenyl unit, and a diphenyl ether linker, all of which were investigated in order to probe the effect of the spacers on the rate of the shuttling process. Data from dynamic 1H NMR spectroscopy revealed a relatively small difference in the ΔG‡ values for the shuttling process in the [2]rotaxanes containing the three different spacers, in contrast to a large difference between the TTF-containing rotaxanes (18 kcalmol-1) and the DNP-containing rotaxanes (15 kcalmol-1). This 3 kcal mol -1 difference is predominantly a result of a ground-state effect, reflecting the much stronger binding of TTF units to the CBPQT4+ ring in comparison with DNP ring systems. An examination of the enthalpic (ΔH‡) and entropic (ΔS‡) components for the shuttling process in the DNP-containing rotaxanes revealed significant differences between the three spacers, a property which could be important in designing new molecules for incorporation into molecular electronic and nanoelectromechanical (NEMs) devices. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | Molecular shuttles | - |
dc.subject | Nanotechnology | - |
dc.subject | NMR spectroscopy | - |
dc.subject | Rotaxanes | - |
dc.subject | Self-assembly | - |
dc.subject | Template synthesis | - |
dc.title | Molecular shuttles based on tetrathiafulvalene units and 1,5-dioxynaphthalene ring systems | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/chem.200305725 | - |
dc.identifier.pmid | 15146527 | - |
dc.identifier.scopus | eid_2-s2.0-2942612847 | - |
dc.identifier.volume | 10 | - |
dc.identifier.issue | 10 | - |
dc.identifier.spage | 2555 | - |
dc.identifier.epage | 2564 | - |
dc.identifier.isi | WOS:000221572900018 | - |