Self-assembly involving hydrogen bonds. Spectral properties and structure of supramolecular complexes of bis-aza-18-crown-6-containing dienones with alkanediammonium salts
[Display omitted] •Complexation of bis-aza-18-crown-6-containing dienones with EtNH3+ and +H3N(CH2)nNH3+.•The stability constants of the supramolecular complexes are measured.•Structures of the complexes are confirmed by 1H NMR spectroscopy and DFT calculations.•Fluorescence is decreased in the pres...
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| Published in | Journal of photochemistry and photobiology. A, Chemistry. Vol. 402; p. 112801 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier B.V
01.11.2020
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| Abstract | [Display omitted]
•Complexation of bis-aza-18-crown-6-containing dienones with EtNH3+ and +H3N(CH2)nNH3+.•The stability constants of the supramolecular complexes are measured.•Structures of the complexes are confirmed by 1H NMR spectroscopy and DFT calculations.•Fluorescence is decreased in the presence of EtNH3+ and +H3N(CH2)nNH3+ (n = 2–8).•Fluorescence is enhanced in the presence of +H3N(CH2)nNH3+ (n = 9, 10, 12).
Dienones (ketocyanine dyes) containing two aza-18-crown-6 ether residues were synthesized. The complex formation of these dyes with the EtNH3+ and +H3N(CH2)nNH3+ ions (n = 2–10, 12) in MeCN was studied by electronic and 1H NMR spectroscopy, including spectrophotometric and 1H NMR titration. It was found that homoditopic bis-azacrown dienones and alkanediammonium ions with a short polymethylene chain form 1:1, 2:2, and 1:2 complexes, whereas alkanediammonium ions with a long polymethylene chain form only pseudocyclic 1:1 complexes. The stability constants of the resulting complexes were determined (logK1:1 varies in the range from 2.74 to 5.62 [M–1], logK2:2 = 2.1 [M–1], and logK1:2 varies in the range from 2.03 to 2.96 [M–1]). The most stable complexes are formed by diammonium ions with a long polymethylene chain owing to simultaneous binding of both NH3+ groups to the azacrown ether residues of the dye. The structure of supramolecular complexes was confirmed by quantum chemical calculations. |
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| AbstractList | [Display omitted]
•Complexation of bis-aza-18-crown-6-containing dienones with EtNH3+ and +H3N(CH2)nNH3+.•The stability constants of the supramolecular complexes are measured.•Structures of the complexes are confirmed by 1H NMR spectroscopy and DFT calculations.•Fluorescence is decreased in the presence of EtNH3+ and +H3N(CH2)nNH3+ (n = 2–8).•Fluorescence is enhanced in the presence of +H3N(CH2)nNH3+ (n = 9, 10, 12).
Dienones (ketocyanine dyes) containing two aza-18-crown-6 ether residues were synthesized. The complex formation of these dyes with the EtNH3+ and +H3N(CH2)nNH3+ ions (n = 2–10, 12) in MeCN was studied by electronic and 1H NMR spectroscopy, including spectrophotometric and 1H NMR titration. It was found that homoditopic bis-azacrown dienones and alkanediammonium ions with a short polymethylene chain form 1:1, 2:2, and 1:2 complexes, whereas alkanediammonium ions with a long polymethylene chain form only pseudocyclic 1:1 complexes. The stability constants of the resulting complexes were determined (logK1:1 varies in the range from 2.74 to 5.62 [M–1], logK2:2 = 2.1 [M–1], and logK1:2 varies in the range from 2.03 to 2.96 [M–1]). The most stable complexes are formed by diammonium ions with a long polymethylene chain owing to simultaneous binding of both NH3+ groups to the azacrown ether residues of the dye. The structure of supramolecular complexes was confirmed by quantum chemical calculations. |
| ArticleNumber | 112801 |
| Author | Freidzon, Alexandra Ya Strelenko, Yuri A. Gromov, Sergey P. Nuriev, Vyacheslav N. Vedernikov, Artem I. Fomina, Marina V. Kurchavov, Nikolai A. |
| Author_xml | – sequence: 1 givenname: Marina V. surname: Fomina fullname: Fomina, Marina V. email: mv_fomina@mail.ru organization: Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow 119421, Russian Federation – sequence: 2 givenname: Nikolai A. surname: Kurchavov fullname: Kurchavov, Nikolai A. email: nakurch@gmail.com organization: Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow 119421, Russian Federation – sequence: 3 givenname: Alexandra Ya orcidid: 0000-0002-7473-7692 surname: Freidzon fullname: Freidzon, Alexandra Ya email: freidzon.sanya@gmail.com organization: Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow 119421, Russian Federation – sequence: 4 givenname: Vyacheslav N. surname: Nuriev fullname: Nuriev, Vyacheslav N. email: nvn@org.chem.msu.ru organization: Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow 119421, Russian Federation – sequence: 5 givenname: Artem I. surname: Vedernikov fullname: Vedernikov, Artem I. email: artem_vedernikov@mail.ru organization: Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow 119421, Russian Federation – sequence: 6 givenname: Yuri A. surname: Strelenko fullname: Strelenko, Yuri A. email: strel@ioc.ac.ru organization: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninskiy prosp. 47, Moscow 119991, Russian Federation – sequence: 7 givenname: Sergey P. orcidid: 0000-0001-9401-7118 surname: Gromov fullname: Gromov, Sergey P. email: spgromov@mail.ru organization: Photochemistry Center of RAS, FSRC “Crystallography and Photonics”, Russian Academy of Sciences, Novatorov str. 7A-1, Moscow 119421, Russian Federation |
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| Keywords | Bis-azacrown-containing dienones Stability constants NMR spectroscopy Quantum chemical calculations Electronic spectroscopy Hydrogen-bonded complexes |
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•Complexation of bis-aza-18-crown-6-containing dienones with EtNH3+ and +H3N(CH2)nNH3+.•The stability constants of the supramolecular... |
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| SubjectTerms | Bis-azacrown-containing dienones Electronic spectroscopy Hydrogen-bonded complexes NMR spectroscopy Quantum chemical calculations Stability constants |
| Title | Self-assembly involving hydrogen bonds. Spectral properties and structure of supramolecular complexes of bis-aza-18-crown-6-containing dienones with alkanediammonium salts |
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