Expanding the Electrochemical Window: New Tunable Aryl Alkyl Ionic Liquids (TAAILs) with Dicyanamide Anions.
dicyanamide anion
electrochemical window
ionic liquids
metal extraction
viscosity
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
18 Dec 2019
18 Dec 2019
Historique:
received:
18
06
2019
revised:
15
08
2019
pubmed:
20
11
2019
medline:
20
11
2019
entrez:
20
11
2019
Statut:
ppublish
Résumé
A set of new tunable aryl alkyl ionic liquids (TAAILs) based on the 1-aryl-3-alkyl imidazolium motif has been synthesized, in which the following variables were systematically changed: alkyl chain length, aryl substitution (group and position), and counter ion. TAAILs with dicyanamide (DCA) and bis(trifluoromethylsulfonyl)imide (N(SO
Identifiants
pubmed: 31743529
doi: 10.1002/chem.201902797
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
16251-16256Subventions
Organisme : Bundesministerium für Bildung und Forschung
ID : 033R141G
Organisme : Deutsche Forschungsgemeinschaft
ID : STR 526/20-1/2
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2002.
A. D. Sawant, D. G. Raut, N. B. Darvatkar, M. M. Salunkhe, Green Chem. Lett. Rev. 2011, 4, 41-54.
V. I. Pârvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615-2665.
P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. 2000, 39, 3772-3789;
Angew. Chem. 2000, 112, 3926-3945.
T. Welton, Green Chem. 2008, 10, 483.
J. Li, S. Yang, W. Wu, H. Jiang, Eur. J. Org. Chem. 2018, 1284-1306.
J. Dupont, L. Kollár, Ionic Liquids (ILs) in Organometallic Catalysis, Springer-Verlag, Berlin Heidelberg, 2015.
H. P. Steinrück, P. Wasserscheid, Catal. Lett. 2015, 145, 380-397.
Y. Huang, G. Luo, M. Huang, J. Wu, Z. Lan, L. Fan, J. Lin, Chem. Rev. 2015, 115, 2136-2173.
M. Gorlov, L. Kloo, Dalton Trans. 2008, 2655-2666.
A. Wang, P. Xing, X. Zheng, H. Cao, G. Yang, X. Zheng, RSC Adv. 2015, 5, 59022-59026.
K. A. Kurnia, C. M. S. S. Neves, M. G. Freire, L. M. N. B. F. Santos, J. A. P. Coutinho, J. Mol. Liq. 2015, 210, 264-271.
M. Rueping, B. J. Nachtsheim, Beilstein J. Org. Chem. 2010, 6, 1-24.
I. L. Odinets, E. V. Sharova, O. I. Artyshin, K. A. Lyssenko, Y. V. Nelyubina, G. V. Myasoedova, N. P. Molochnikova, E. A. Zakharchenro, Dalton Trans. 2010, 39, 4170.
A. Muhammad, M. I. Abdul Mutalib, C. D. Wilfred, T. Murugesan, A. Shafeeq, J. Chem. Thermodyn. 2008, 40, 1433-1438.
I. M. Riddlestone, A. Kraft, J. Schaefer, I. Krossing, Angew. Chem. Int. Ed. 2018, 57, 13982-14024;
Angew. Chem. 2018, 130, 14178-14221.
N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123-150.
M. L. Dietz, Sep. Sci. Technol. 2006, 41, 2047-2063.
G. T. Wei, Z. Yang, C. J. Chen, Anal. Chim. Acta 2003, 488, 183-192.
H. Zhao, S. Xia, P. Ma, J. Chem. Technol. Biotechnol. 2005, 80, 1089-1096.
D. Depuydt, A. Van Den Bossche, W. Dehaen, K. Binnemans, Chem. Commun. 2017, 53, 5271-5274.
A. E. Visser, R. P. Swatloski, W. M. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J. James, H. Davis, R. D. Rogers, Chem. Commun. 2001, 135-136.
D. Parmentier, S. Paradis, S. J. Metz, S. K. Wiedmer, M. C. Kroon, Chem. Eng. Res. Des. 2016, 109, 553-560.
D. Dupont, K. Binnemans, Green Chem. 2015, 17, 2150-2163.
C. H. C. Janssen, N. A. Macías-Ruvalcaba, M. Aguilar-Martínez, M. N. Kobrak, Int. Rev. Phys. Chem. 2015, 34, 591-622.
M. Gras, N. Papaiconomou, N. Schaeffer, E. Chainet, F. Tedjar, J. A. P. Coutinho, I. Billard, Angew. Chem. Int. Ed. 2018, 57, 1563-1566;
Angew. Chem. 2018, 130, 1579-1582.
M. J. Deng, I. W. Sun, P. Y. Chen, J. K. Chang, W. T. Tsai, Electrochim. Acta 2008, 53, 5812-5818.
S. Zein El Abedin, F. Endres, ChemPhysChem 2006, 7, 58-61.
M. J. Deng, P. Y. Chen, T. I. Leong, I. W. Sun, J. K. Chang, W. T. Tsai, Electrochem. Commun. 2008, 10, 213-216.
N.-C. Lo, P.-C. Chung, W.-J. Chuang, S. C. N. Hsu, I.-W. Sun, P.-Y. Chen, J. Electrochem. Soc. 2016, 162, D9-D16.
A. P. Abbott, G. Frisch, J. Hartley, K. S. Ryder, Green Chem. 2011, 13, 471-481.
M. Antonietti, D. Kuang, B. Smarsly, Y. Zhou, Angew. Chem. Int. Ed. 2004, 43, 4988-4992;
Angew. Chem. 2004, 116, 5096-5100.
C. Vollmer, E. Redel, K. Abu-Shandi, R. Thomann, H. Manyar, C. Hardacre, C. Janiak, Chem. Eur. J. 2010, 16, 3849-3858.
A. Taubert, Z. Li, Dalton Trans. 2007, 723-727.
C. Janiak, Z. Naturforsch., B J. Chem. Sci. 2013, 68, 1059-1089.
Y. Han, D. Qiao, L. Sun, D. Feng, Tribol. Int. 2018, 119, 766-774.
S. Kawada, S. Watanabe, C. Tadokoro, R. Tsuboi, S. Sasaki, Tribol. Int. 2018, 119, 474-480.
Q. Yang, L. Wang, Z. Zhou, L. Wang, Y. Zhang, S. Zhao, G. Dong, Y. Cheng, T. Min, Z. Hu, W. Chen, K. Xia, M. Liu, Nat. Commun. 2018, 9, 991.
H. Tokuda, K. Hayamizu, K. Ishii, M. A. B. H. Susan, M. Watanabe, J. Phys. Chem. B 2004, 108, 16593-16600.
H. Tokuda, K. Hayamizu, K. Ishii, M. A. B. H. Susan, M. Watanabe, J. Phys. Chem. B 2005, 109, 6103-6110.
S. Ahrens, A. Peritz, T. Strassner, Angew. Chem. Int. Ed. 2009, 48, 7908-7910;
Angew. Chem. 2009, 121, 8048-8051.
D. Meyer, T. Strassner, J. Org. Chem. 2011, 76, 305-308.
T. Schulz, S. Ahrens, D. Meyer, C. Allolio, A. Peritz, T. Strassner, Chem. Asian J. 2011, 6, 863-867.
M. Kaliner, A. Rupp, I. Krossing, T. Strassner, Chem. Eur. J. 2016, 22, 10044-10049.
L. Schmolke, S. Lerch, M. Bülow, M. Siebels, A. Schmitz, J. Thomas, G. Dehm, C. Held, T. Strassner, C. Janiak, Nanoscale 2019, 11, 4073-4082.
T. Schulz, T. Strassner, J. Organomet. Chem. 2013, 744, 113-1118.
F. Schroeter, S. Lerch, M. Kaliner, T. Strassner, Org. Lett. 2018, 20, 6215-6219.
F. Schroeter, J. Soellner, T. Strassner, Chem. Eur. J. 2019, 25, 2527-2537.
D. R. MacFarlane, J. Golding, S. Forsyth, M. Forsyth, G. B. Deacon, Chem. Commun. 2001, 1430-1431.
D. R. MacFarlane, S. A. Forsyth, J. Golding, G. B. Deacon, Green Chem. 2002, 4, 444-448.
Y. Yoshida, O. Baba, G. Saito, J. Phys. Chem. B 2007, 111, 4742-4749.
K. Tsunashima, S. Kodama, M. Sugiya, Y. Kunugi, Electrochim. Acta 2010, 56, 762-766.
W.-L. Yuan, X. Yang, L. He, Y. Xue, S. Qin, G.-H. Tao, Front. Chem. 2018, 6, 1-12.
S. Boudesocque, A. Mohamadou, L. Dupont, A. Martinez, I. Déchamps, RSC Adv. 2016, 6, 107894-107904.
C. Lian, H. Liu, C. Li, J. Wu, AIChE J. 2019, 65, 804-810.
S. P. Ong, O. Andreussi, Y. Wu, N. Marzari, G. Ceder, Chem. Mater. 2011, 23, 2979-2986.
S. Kazemiabnavi, Z. Zhang, K. Thornton, S. Banerjee, J. Phys. Chem. B 2016, 120, 5691-5702.
M. Hayyan, F. S. Mjalli, M. A. Hashim, I. M. AlNashef, T. X. Mei, J. Ind. Eng. Chem. 2013, 19, 106-112.
M. P. S. Mousavi, B. E. Wilson, S. Kashefolgheta, E. L. Anderson, S. He, P. Bühlmann, A. Stein, ACS Appl. Mater. Interfaces 2016, 8, 3396-3406.
A. Lewandowski, I. Stépniak, Phys. Chem. Chem. Phys. 2003, 5, 4215-4218.
M. Galiński, A. Lewandowski, I. Stepniak, Electrochim. Acta 2006, 51, 5567-5580.
A. M. O′Mahony, D. S. Silvester, L. Aldous, C. Hardacre, R. G. Compton, J. Chem. Eng. Data 2008, 53, 2884-2891.
Q. Li, J. Jiang, G. Li, W. Zhao, X. Zhao, T. Mu, Sci. China Chem. 2016, 59, 571-577.
T. Hmissa, X. Zhang, N. R. Dhumal, G. J. McManus, X. Zhou, H. B. Nulwala, A. Mirjafari, Angew. Chem. Int. Ed. 2018, 57, 16005-16009;
Angew. Chem. 2018, 130, 16237-16241.
A. Rupp, N. Roznyatovskaya, H. Scherer, W. Beichel, P. Klose, C. Sturm, A. Hoffmann, J. Tübke, T. Koslowski, I. Krossing, Chem. Eur. J. 2014, 20, 9794-9804.
C. M. S. S. Neves, K. A. Kurnia, J. A. P. Coutinho, I. M. Marrucho, J. N. C. Lopes, M. G. Freire, L. P. N. Rebelo, J. Phys. Chem. B 2013, 117, 10271-10283.