Solvent-Triggered Long-Range Proton Transport in 7-Hydroxyquinoline Using a Sulfonamide Transporter Group
- Kosuke Nakashima*Kosuke Nakashima*Email: [email protected]Department of Pharmaceutical Chemistry, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, JapanMore by Kosuke Nakashima
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- Anton Georgiev*Anton Georgiev*Email: [email protected]Department of Organic Chemistry, University of Chemical Technology and Metallurgy, 8 St. Kliment Ohridski Boulevard, 1756 Sofia, BulgariaInstitute of Electronics, Bulgarian Academy of Sciences, 72 Tzarigradsko Chaussee Boulevard, 1784 Sofia, BulgariaInstitute of Optical Materials and Technologies, Bulgarian Academy of Sciences, Acad. G. Bonchev Avenue, Building 109, 1113 Sofia, BulgariaMore by Anton Georgiev
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- Dancho YordanovDancho YordanovInstitute of Electronics, Bulgarian Academy of Sciences, 72 Tzarigradsko Chaussee Boulevard, 1784 Sofia, BulgariaInstitute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev Avenue, Building 9, Sofia 1113, BulgariaMore by Dancho Yordanov
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- Yasuyuki MatsushimaYasuyuki MatsushimaDepartment of Pharmaceutical Chemistry, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, JapanMore by Yasuyuki Matsushima
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- Shin-ichi HirashimaShin-ichi HirashimaDepartment of Pharmaceutical Chemistry, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, JapanMore by Shin-ichi Hirashima
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- Tsuyoshi MiuraTsuyoshi MiuraDepartment of Pharmaceutical Chemistry, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, JapanMore by Tsuyoshi Miura
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- Liudmil Antonov*Liudmil Antonov*Email: [email protected]Department of Organic Chemistry, University of Chemical Technology and Metallurgy, 8 St. Kliment Ohridski Boulevard, 1756 Sofia, BulgariaInstitute of Electronics, Bulgarian Academy of Sciences, 72 Tzarigradsko Chaussee Boulevard, 1784 Sofia, BulgariaMore by Liudmil Antonov
Abstract
The ability of long-range proton transport by substitution of 7-hydroxyquinoline at the eighth position with sulfonamide and sulfonylhydrazone rotor units to act as a crane-arm has been studied. Different proton transport pathways triggered by different stimuli have been established depending on the structure of the crane-arms. Solvent-driven proton switching from OH to the quinoline nitrogen (Nquin) site, facilitated by a sulfonamide transporter group in polar protic and aprotic solvents, has been confirmed by optical (absorption and fluorescence) and NMR spectroscopies as well as by single-crystal X-ray structure analysis. Photoinduced long-range proton transport to the Nquin site upon 340 nm UV light irradiation has been estimated in sulfonylhydrazone, which is not sensitive to solvent-driven switching. Both compounds have exhibited acid-triggered switching by trifluoroacetic acid due to the formation of a stable six-membered intramolecular hydrogen bonding interaction between the protonated Nquin and crane-arm. The structures of acid-switched form were confirmed by NMR spectroscopy and single-crystal X-ray structure analysis. The behavior of the compounds suggests a big step forward in the advanced proton pump-switching architecture because they cover three distinct driving forces in the switching process: solvent, light, and acid.
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