A macrocyclic receptor containing two viologen species connected by conjugated terphenyl groups
A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular N center dot center dot center dot N separation of ca. 7.4 angstrom....
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| Vydáno v: | Organic & biomolecular chemistry Ročník 16; číslo 27; s. 5006 - 5015 |
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| Hlavní autoři: | , , , , , , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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Royal Soc Chemistry
2018
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| ISSN: | 1477-0520, 1477-0539, 1477-0539 |
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| Abstract | A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular N center dot center dot center dot N separation of ca. 7.4 angstrom. Thus, the internal cavity dimensions are suitable for the inclusion of pi-electron-rich species. The macrocycle is redox active, and can accept electrons from suitable donor species including triethylamine, resulting in a dramatic colour change from pale yellow to dark green as a consequence of the formation of a paramagnetic bis(radical cationic) species. Cyclic voltammetry shows that the macrocycle can undergo two sequential and reversible reduction processes (E-1/2 = -0.65 and -0.97 V vs. Fc/Fc(+)). DFT and TD-DFT studies accurately replicate the structure of the tetracationic macrocycle and the electronic absorption spectra of the three major redox states of the system. These calculations also showed that during electrochemical reduction, the unpaired electron density of the radical cations remained relatively localised within the heterocyclic rings. The ability of the macrocycle to form supramolecular complexes was confirmed by the formation of a pseudorotaxane with a guest molecule containing a p-electron-rich 1,5-dihydroxynaphthalene derivative. Threading and dethreading of the pseudorotaxane was fast on the NMR timescale, and the complex exhibited an association constant of 150 M-1 (+/- 30 M-1) as calculated from H-1 NMR titration studies. |
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| AbstractList | A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular NN separation of ca. 7.4 Å. Thus, the internal cavity dimensions are suitable for the inclusion of π-electron-rich species. The macrocycle is redox active, and can accept electrons from suitable donor species including triethylamine, resulting in a dramatic colour change from pale yellow to dark green as a consequence of the formation of a paramagnetic bis(radical cationic) species. Cyclic voltammetry shows that the macrocycle can undergo two sequential and reversible reduction processes (E1/2 = -0.65 and -0.97 V vs. Fc/Fc+). DFT and TD-DFT studies accurately replicate the structure of the tetracationic macrocycle and the electronic absorption spectra of the three major redox states of the system. These calculations also showed that during electrochemical reduction, the unpaired electron density of the radical cations remained relatively localised within the heterocyclic rings. The ability of the macrocycle to form supramolecular complexes was confirmed by the formation of a pseudorotaxane with a guest molecule containing a π-electron-rich 1,5-dihydroxynaphthalene derivative. Threading and dethreading of the pseudorotaxane was fast on the NMR timescale, and the complex exhibited an association constant of 150 M-1 (±30 M-1) as calculated from 1H NMR titration studies. A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular N center dot center dot center dot N separation of ca. 7.4 angstrom. Thus, the internal cavity dimensions are suitable for the inclusion of pi-electron-rich species. The macrocycle is redox active, and can accept electrons from suitable donor species including triethylamine, resulting in a dramatic colour change from pale yellow to dark green as a consequence of the formation of a paramagnetic bis(radical cationic) species. Cyclic voltammetry shows that the macrocycle can undergo two sequential and reversible reduction processes (E-1/2 = -0.65 and -0.97 V vs. Fc/Fc(+)). DFT and TD-DFT studies accurately replicate the structure of the tetracationic macrocycle and the electronic absorption spectra of the three major redox states of the system. These calculations also showed that during electrochemical reduction, the unpaired electron density of the radical cations remained relatively localised within the heterocyclic rings. The ability of the macrocycle to form supramolecular complexes was confirmed by the formation of a pseudorotaxane with a guest molecule containing a p-electron-rich 1,5-dihydroxynaphthalene derivative. Threading and dethreading of the pseudorotaxane was fast on the NMR timescale, and the complex exhibited an association constant of 150 M-1 (+/- 30 M-1) as calculated from H-1 NMR titration studies. A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular NN separation of ca. 7.4 Å. Thus, the internal cavity dimensions are suitable for the inclusion of π-electron-rich species. The macrocycle is redox active, and can accept electrons from suitable donor species including triethylamine, resulting in a dramatic colour change from pale yellow to dark green as a consequence of the formation of a paramagnetic bis(radical cationic) species. Cyclic voltammetry shows that the macrocycle can undergo two sequential and reversible reduction processes (E1/2 = -0.65 and -0.97 V vs. Fc/Fc+). DFT and TD-DFT studies accurately replicate the structure of the tetracationic macrocycle and the electronic absorption spectra of the three major redox states of the system. These calculations also showed that during electrochemical reduction, the unpaired electron density of the radical cations remained relatively localised within the heterocyclic rings. The ability of the macrocycle to form supramolecular complexes was confirmed by the formation of a pseudorotaxane with a guest molecule containing a π-electron-rich 1,5-dihydroxynaphthalene derivative. Threading and dethreading of the pseudorotaxane was fast on the NMR timescale, and the complex exhibited an association constant of 150 M-1 (±30 M-1) as calculated from 1H NMR titration studies.A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal X-ray structure shows that the two viologen residues have a transannular NN separation of ca. 7.4 Å. Thus, the internal cavity dimensions are suitable for the inclusion of π-electron-rich species. The macrocycle is redox active, and can accept electrons from suitable donor species including triethylamine, resulting in a dramatic colour change from pale yellow to dark green as a consequence of the formation of a paramagnetic bis(radical cationic) species. Cyclic voltammetry shows that the macrocycle can undergo two sequential and reversible reduction processes (E1/2 = -0.65 and -0.97 V vs. Fc/Fc+). DFT and TD-DFT studies accurately replicate the structure of the tetracationic macrocycle and the electronic absorption spectra of the three major redox states of the system. These calculations also showed that during electrochemical reduction, the unpaired electron density of the radical cations remained relatively localised within the heterocyclic rings. The ability of the macrocycle to form supramolecular complexes was confirmed by the formation of a pseudorotaxane with a guest molecule containing a π-electron-rich 1,5-dihydroxynaphthalene derivative. Threading and dethreading of the pseudorotaxane was fast on the NMR timescale, and the complex exhibited an association constant of 150 M-1 (±30 M-1) as calculated from 1H NMR titration studies. |
| Author | Evans, Robert Lim, Kate J. C. Pizl, Martin Greenland, Barnaby W. Chen, Long Chippindale, Ann M. Colquhoun, Howard M. Hartl, Frantisek Taylor, James O. Babra, Tahkur S. |
| Author_xml | – sequence: 1 givenname: Long surname: Chen fullname: Chen, Long organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 2 givenname: Kate J. C. surname: Lim fullname: Lim, Kate J. C. organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 3 givenname: Tahkur S. orcidid: 0000-0002-1638-7508 surname: Babra fullname: Babra, Tahkur S. organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 4 givenname: James O. surname: Taylor fullname: Taylor, James O. organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 5 givenname: Martin orcidid: 0000-0003-4990-9218 surname: Pizl fullname: Pizl, Martin organization: Acad Sci Czech Republ, J Heyrovsky Inst Phys Chem, Dolejskova 3, CZ-18223 Prague, Czech Republic – sequence: 6 givenname: Robert orcidid: 0000-0003-1471-201X surname: Evans fullname: Evans, Robert organization: Aston Univ, Inst Mat Res, Sch Engn & Appl Sci, Birmingham B4 7ET, W Midlands, England – sequence: 7 givenname: Ann M. surname: Chippindale fullname: Chippindale, Ann M. organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 8 givenname: Frantisek orcidid: 0000-0002-7013-5360 surname: Hartl fullname: Hartl, Frantisek organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 9 givenname: Howard M. surname: Colquhoun fullname: Colquhoun, Howard M. email: h.m.colquhoun@reading.ac.uk organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England – sequence: 10 givenname: Barnaby W. surname: Greenland fullname: Greenland, Barnaby W. email: b.w.greenland@sussex.ac.uk organization: Univ Reading, Dept Chem, Reading RG6 6AD, Berks, England |
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| Keywords | STACKING POLYMERS NMR CONDUCTIVITY CONVECTION RADICAL CATIONS CRYSTAL-STRUCTURES SUPRAMOLECULAR CHEMISTRY COMPLEXATION MOLECULES |
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| Snippet | A macrocyclic receptor molecule containing two viologen species connected by conjugated terphenyl groups has been designed and synthesised. The single-crystal... |
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| Title | A macrocyclic receptor containing two viologen species connected by conjugated terphenyl groups |
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