Abstract
The synthesis and ion-binding properties of amide-based derivative of embonic acid andp-aminoazobenzenewere described. The new compound was characterized by X-ray structural analysis and spectroscopic methods.Ligand interacts in acetonitrile with Y-shaped anions (benzoates and acetates) and dihydrogen phosphatesforming complexes of 1:1 stoichiometry. In more polar DMSO the complexes stoichiometry changes to 2:1(L:anion). Light-inducedtranstocisisomerization was studied. The effect of anions on thermal back iso-merization was investigated.
Citations
-
8
CrossRef
-
0
Web of Science
-
7
Scopus
Authors (5)
Cite as
Full text
download paper
downloaded 72 times
- Publication version
- Accepted or Published Version
- License
- open in new tab
Keywords
Details
- Category:
- Articles
- Type:
- artykuły w czasopismach
- Published in:
-
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
no. 390,
ISSN: 1010-6030 - Language:
- English
- Publication year:
- 2020
- Bibliographic description:
- Łukasik N., Chojnacki J., Luboch E., Okuniewski A., Wagner-Wysiecka E.: Photoresponsive, amide-based derivative of embonic acid for anion recognition// JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY -Vol. 390, (2020), s.112307-
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.jphotochem.2019.112307
- Bibliography: test
-
- N. Pankratova, M. Cuartero, L.A. Jowett, E.N.W. Howe, P.A. Gale, E. Bakker, G.A. Crespo, Fluorinated tripodal receptors for potentiometric chloride detection in biological fluids, Biosens. open in new tab
- Bioelectron. 99 (2018) 70-76; b) N. Łukasik, E. Wagner-Wysiecka, A. Małachowska, Iron(III)-selective materials based on a catechol-bearing amide for optical sensing, Analyst 144 (2019) 3119-3127. open in new tab
- V. Soto-Cerrato, P. Manuel-Manresa, E. Hernando, S. Calabuig-Fariñas, A. Martínez-Romero, V. open in new tab
- Fernández-Dueñas, K. Sahlholm, T. Knöpfel, M. García-Valverde, A.M. Rodilla, E. Jantus-Lewintre,
- R. Farràs, F. Ciruela, R. Pérez-Tomás, R. Quesada, Facilitated anion transport induces hyperpolarization of the cell membrane that triggers differentiation and cell death in cancer stem cells, J. Am. Chem. Soc. 137 (2015) 15892-15898; b) N. Busschaert, S.-H. Park, K.-H. Baek, Y.P. Choi, J. Park, E.N.W. Howe, J.R. Hiscock, L.E. Karagiannidis, I. Marques, V. Félix, W. Namkung, J.L. Sessler, P.A. Gale, I. Shin, A synthetic ion transporter that disrupts autophagy and induces apoptosis by perturbing cellular chloride concentrations, Nat. Chem. 9 (2017) 667-675.
- T. Ito, Y. Xu, S.Y. Kim, R. Nagaishi, T. Kimura, Adsorption behavior and radiation effects of a silica-based (calix(4)+ dodecanol)/SiO2-P adsorbent for selective separation of Cs(I) from high level liquid waste, Separ. Sci. Technol. 51 (2016) 22-31; b) I. Rais, S. Tachimori, E. Yoo, J. Alexova, M. open in new tab
- Bubenikova, Extraction of radioactive Cs and Sr from nitric acid solutions with 25,27-bis(1- octyloxy)calix[4]-26,28-crown-6 and dicyclohexyl-18-crown-6: effect of nature of the organic solvent, Separ. Sci. Technol. 50 (2015) 1202-1212.
- S. Lee, A.H. Flood, Photoresponsive receptors for binding and releasing anions, J. Phys. Org. open in new tab
- Chem. 26 (2013) 79-86; b) M. Natali, S. Giordani, Molecular switches as photocontrollable "smart" receptors, Chem. Soc. Rev. 41 (2012) 4010-4029. open in new tab
- a) S.S. Deshpande, M.A. Jachak, S.S. Khopkar, G.S. Shankarling, A simple substituted spiropyran acting as a photo reversible switch for the detection of lead (Pb2+) ions, Sensor Actuat. B-Chem. 258 (2018) 648-656; b) S. Heng, A.M. Mak, R. Kostecki, X. Zhang, J. Pei, D.B. Stubing, H. Ebendorff- open in new tab
- Heidepriem, A.D. Abell, Photoswitchable calcium sensor: 'On'-'Off' sensing in cells or with microstructured optical fibers, Sensor Actuat. B-Chem. 252 (2017) 965-972.
- H. Ding, B. Li, S. Pu, G. Liu, D. Jia, Y. Zhou, A fluorescent sensor based on a diarylethene- rhodamine derivative for sequentially detecting Cu 2+ and arginine and its application in keypad lock, Sensor Actuat. B-Chem. 247 (2017) 26-35; b) F. Liu, C. Fan, S. Pu, A new "turn-on" fluorescent chemosensor for Zn2+ based on a diarylethene derivative and its practical applications, J. Photochem. Photobiol. A: Chem. 371 (2019) 248-254. open in new tab
- A.A. Beharry, G.A. Woolley, Azobenzene photoswitches for biomolecules, Chem. Soc. Rev. 40 (2011) 4422-4437; b) E. Wagner-Wysiecka, N. Łukasik, J.F. Biernat, E. Luboch, Azo group(s) in selected macrocyclic compounds, J. Incl. Phenom. Macrocycl. Chem. 90 (2018) 189-257.
- J. García-Amorós, D. Velasco, Recent advances towards azobenzene-based light-driven real-time information-transmitting materials, Beilstein J. Org. Chem. 8 (2012) 1003-1017. open in new tab
- T. Gao, Y. Xue, Z. Zhang, W. Que, Multi-wavelength optical data processing and recording based on azo-dyes doped organic-inorganic hybrid film, Opt. Express 26 (2018) 4309-4317. open in new tab
- A. Babalhavaeji, G. A. Woolley, Modular design of optically controlled protein affinity reagents, Chem. Comm. 54 (2018) 1591-1594. open in new tab
- L. Stricker, M. Böckmann, T.M. Kirse, N.L. Doltsinis, B.J. Ravoo, Arylazopyrazole photoswitches in aqueous solution: substituent effects, photophysical properties, and host-guest chemistry, Chem. Eur. open in new tab
- J. 24 (2018) 8639-8647. open in new tab
- K. Dąbrowa, P. Niedbała, J. Jurczak, Anion-tunable control of thermal Z→E isomerisation in basic azobenzene receptors, Chem. Comm. 50 (2014) 15748-15751. open in new tab
- Y.R. Choi, G.C. Kim, H.-G. Joen, J. Park, W. Namkung, K.-S. Jeong, Azobenzene-based chloride transporters with light-controllable activities, Chem. Comm. 50 (2014) 15305-15308. open in new tab
- J.B. Nanubolu, B. Sridhar, K. Ravikumar, K.D. Sawant, T.A. Naik, L.N. Patkar, S. Cherukuvada, B. Sreedhar, Polymorphism in metformin embonate salt -recurrence of dimeric and tetrameric guanidinium-carboxylate synthons, CrystEngComm 15 (2013) 4448-4464. open in new tab
- J. Bernstein, R.E. Davis, L. Shimoni, N.-L. Chang, Patterns in hydrogen bonding functionality and graph set analysis in crystals, Angew. Chem. Int. Ed. 34 (1995) 1555-1573. open in new tab
- GaussView, Version 5.0.9, Roy Dennington, Todd A. Keith, and John M. Millam, Semichem Inc., Shawnee Mission, KS, 2016.
- C. Pérez-Casas, A. K. Yatsimirsky, Detailing hydrogen bonding and deprotonation equilibria between anions and urea/thiourea derivatives, J. Org. Chem. 73 (2008) 2275-2284; b) V. Amendola, G. open in new tab
- Bergamaschi, M. Boiocchi, L. Fabbrizzi, M. Milani, The squaramide versus urea contest for anion recognition, Chem. Eur. J. 16 (2010) 4368-4380.
- A. Sarkar, S. Bhattacharyya, A. Mukherjee, Colorimetric detection of fluoride ions by anthraimidazoledione based sensors in the presence of Cu(II) ions, Dalton Trans. 45 (2016) 1166-1175; open in new tab
- b) E. Wagner-Wysiecka, J. Chojnacki, Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors, Supramol. Chem. 24 (2012) 684-695. open in new tab
- K. Alizadeh, B. Rezaei and E. Khazaeli, A new triazene-1-oxide derivative, immobilized on the triacetyl cellulose membrane as an optical Ni 2+ sensor, Sensor Acuat. B-Chem. 193 (2014) 267-272; (b) open in new tab
- N. Łukasik, E. Wagner-Wysiecka, Salicylaldimine-based receptor as a material for iron(III) selective optical sensing, J. Photochem. Photobiol. A-Chem. 346 (2017) 318-326. open in new tab
- M. Müri, K.C. Schuermann, L. De Cola, M. Mayor, Shape-switchable azo-macrocycles, Eur. J. Org. Chem. (2009) 2562-2575; b) N. Łukasik, E. Wagner-Wysiecka, Anion binding by p- aminoazobenzene-derived aromatic amides: spectroscopic and electrochemical studies, Photochem. Photobiol. Sci. 16 (2017) 1570-1579.
- K. Dąbrowa, J. Jurczak, Tetra-(meta-butylcarbamoyl)azobenzene: a rationally designed photoswitch with binding affinity for oxoanions in a long-lived Z-state, Org. Lett. 19 (2017) 1378-1381. open in new tab
- STOE &Cie GmbH, X-Area 1.75, STOE &Cie GmbH, Darmstadt, Germany, 2015. open in new tab
- G.M. Sheldrick, A short history of SHELX, Acta Cryst. A64 (2008) 112-122. open in new tab
- G.M. Sheldrick, Crystal structure refinement with SHELXL, Acta Cryst. C71 (2015) 3-8.
- O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J. A.K. Howard, H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program, J. Appl. Cryst. 42 (2009) 339-341. open in new tab
- Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F.
- Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A.
- Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. open in new tab
- Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A.
- Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
- M. Kyvala, I. Lukeš, program package "OPIUM" available (free of charge) at http://www.natur.cuni.cz/~kyvala/opium.html
- Sources of funding:
-
- Statutory activity/subsidy
- Verified by:
- Gdańsk University of Technology
seen 153 times
Recommended for you
Azo group(s) in selected macrocyclic compounds
- E. Wagner-Wysiecka,
- N. Łukasik,
- J. Biernat
- + 1 authors
2018
Photoresponsive Amide-Based Derivatives of Azobenzene-4,4′-Dicarboxylic Acid—Experimental and Theoretical Studies
- N. Łukasik,
- K. Hemine,
- I. Anusiewicz
- + 2 authors
2021