15-crown-5 ether; Co catalysts; Crown-ethers; Free ions; Ion pairs; Lactides; On demands; Photo-switchable; Potassium acetate; UV-light; Catalysis
Abstract :
[en] An azobenzene-bridged 15-crown-5 ether (1) was successfully used as a photoswitchable cocatalyst for modulating the catalytic activity of potassium acetate (KOAc) in the ring-opening polymerization (ROP) ofl-lactide (l-LA) when initiated from an exogenous alcohol. By alternating exposure to daylight and UV light,1transforms the K+−OAc ion pair-like in free ions “on-demand”, resulting in an effective form of the catalytic complex. This allows the modulation of thel-LA ROP speed, switching the process from a slow to a fast state.
Disciplines :
Chemistry
Author, co-author :
De Roover, Quentin; Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, Mons, Belgium ; Organic Synthesis and Mass Spectrometry Laboratory (S2MOs), Materials Institute, Mons, Belgium
Vucko, Timothé; Unité de Chimie Organique, Université de Namur ASBL, Namur, Belgium
{"lastName":"Vincent", "firstNames":"Stéphane P.","affiliations":["Unité de Chimie Organique, Université de Namur ASBL, Namur, Belgium"],"ids":["SC:7202465314""OR:0000-0001-6258-9058"]}
Research Institute for Materials Science and Engineering
Funders :
Fonds De La Recherche Scientifique - FNRS H2020 Marie Skłodowska-Curie Actions
Funding text :
This work was support by the Research and Innovation Staff Exchange (RISE) BIODEST H2020-MSCA-RISE-2017-778092 project. O. C. is Senior Research Associate for the F.R.S.-FNRS. T. V. is grateful to the FNRS for PDR T.0102.18 financement.
F. A. Leibfarth, K. M. Mattson, B. P. Fors, H. A. Collins, C. J. Hawker, Angew. Chem. Int. Ed. 2013, 52, 199
C. K. Ober, S. Z. D. Cheng, P. T. Hammond, M. Muthukumar, E. Reichmanis, K. L. Wooley, T. P. Lodge, Macromolecules, 2009, 42, 465
D. J. Walsh, M. G. Hyatt, S. A. Miller, D. Guironnet, ACS Catal. 2019, 9, 11153
R. Göstl, A. Senf, S. Hecht, Chem. Soc. Rev. 2014, 43, 1982
X. Sun, J. P. Gao, Z. Y. Wang, J. Am. Chem. Soc. 2008, 130, 8130
B. M. Neilson, C. W. Bielawski, Chem. Commun. 2013, 49, 5453
I. A. Barker, A. P. Dove, Chem. Commun. 2013, 49, 1205
C. Fu, J. Xu, C. Boyer, Chem. Commun. 2016, 52, 7126
Z. Dai, Y. Cui, C. Chen, J. Wu, Chem. Commun. 2016, 52, 8826
A. J. Teator, H. Shao, G. Lu, P. Liu, C. W. Bielawski, Organometallics, 2017, 36, 490
F. Eisenreich, M. Kathan, A. Dallmann, S. P. Ihrig, T. Schwaar, B. M. Schmidt, S. Hecht, Nat. Catal. 2018, 1, 516
P. K. Kuroishi, A. P. Dove, Chem. Commun. 2018, 54, 6264
M. Li, P. Zhang, C. Chen, Macromolecules, 2019, 52, 5646
S. Kaler, P. McKeown, B. D. Ward, M. D. Jones, Inorg. Chem. Front. 2021, 8, 711
S. Moins, Q. De Roover, C. Henoumont, S. Laurent, J. De Winter, O. Coulembier, Catal. Sci. Technol. 2021, 11, 4387
K. H. Wong, M. Bourgein, J. Smid, J. Chem. Soc. Chem. Commun. 1974, 715
M. Bourgoin, K. H. Wong, J. Y. Hui, J. Smid, J. Am. Chem. Soc. 1975, 97, 3462
R. Ungaro, B. E. Haj, J. Smid, J. Am. Chem. Soc. 1976, 98, 5198
K. Kimura, H. Tamura, T. Tsuchida, T. Shono, Chem. Lett. 1979, 611
S. Shinkai, T. Nakaji, T. Ogawa, K. Shigematsu, O. Manabe, J. Am. Chem. Soc. 1981, 103, 111
N. A. Noureldin, J. W. Bellegarde, Synthesis, 1999, 6, 939
O. Coulembier, A. P. Dove, R. C. Pratt, A. C. Sentman, D. A. Culkin, L. Mespouille, P. Dubois, R. M. Waymouth, J. L. Hedrick, Angew. Chem. Int. Ed. 2005, 44, 2
O. Coulembier, P. Dubois, J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 1672
M. Kawalec, O. Coulembier, P. Gerbaux, M. Sobota, J. De Winter, P. Dubois, M. Kowalczuk, P. Kurcok, React. Funct. Polym. 2012, 72, 509
A. Warshawsky, N. Kahana, J. Am. Chem. Soc. 1982, 104, 2663
C. Ozen, T. Satoh, S. Maeda, J. Comput. Chem. 2020, 41, 2197