Tunable Hydrogen Release from Amine-Boranes via their Insertion into Functional Polystyrenes.
Lewis pairs
amine-boranes
boron
dehydrogenation
polymers
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
21 Oct 2019
21 Oct 2019
Historique:
received:
19
04
2019
revised:
10
07
2019
pubmed:
7
8
2019
medline:
7
8
2019
entrez:
7
8
2019
Statut:
ppublish
Résumé
Polystyrene-g-boramine random copolymers are dihydrogen reservoirs with tunable dehydrogenation temperatures, which can be adjusted by selecting the boramine content in the copolymers. They display a unique dihydrogen thermal release profile, which is a direct consequence of the insertion of the amine-boranes in a polymeric scaffold, and not from a direct modification of the electronics or sterics of the amine-borane function. Finally, the mixture of polystyrene-g-boramines with conventional NH
Identifiants
pubmed: 31386245
doi: 10.1002/anie.201904898
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
15239-15243Subventions
Organisme : Agence Nationale de la Recherche
ID : 10.13039/501100001665, NHCX
Organisme : Université Claude Bernard Lyon 1
ID : DOI: 10.13039/501100006687
Organisme : Centre National de la Recherche Scientifique
ID : DOI: 10.13039/501100004794
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
A. Staubitz, A. P. M. Robertson, I. Manners, Chem. Rev. 2010, 110, 4079-4124.
Z. Mo, A. Rit, J. Campos, E. L. Kolychev, S. Aldridge, J. Am. Chem. Soc. 2016, 138, 3306-3309;
A. Khalily, H. Eren, S. Akbayrak, H. H. Susapto, N. Biyikli, S. M. O. Guler, Angew. Chem. Int. Ed. 2016, 55, 12257-12261;
Angew. Chem. 2016, 128, 12445-12449;
Z. Lu, L. Schweighauser, H. Hausmann, H. A. Wegner, A. Hermann, Angew. Chem. Int. Ed. 2015, 54, 15556-15559;
Angew. Chem. 2015, 127, 15777-15780;
X. Hu, M. Soleilhavoup, M. Melaimi, J. Chu, G. Bertrand, Angew. Chem. Int. Ed. 2015, 54, 6008-6011;
Angew. Chem. 2015, 127, 6106-6109;
B. L. Conley, D. Guess, T. J. Williams, J. Am. Chem. Soc. 2011, 133, 14212-14215;
R. J. Keaton, J. M. Blacquiere, R. T. Baker, J. Am. Chem. Soc. 2007, 129, 1844-1845;
M. C. Denney, V. Pons, T. J. Hebden, M. D. Heinekey, K. I. Goldberg, J. Am. Chem. Soc. 2006, 128, 12048-12049; for dehydrocouplings, see:
J. R. Vance, A. Schafer, A. P. M. Robertson, K. Lee, J. Turner, G. R. Whittell, I. Manners, J. Am. Chem. Soc. 2014, 136, 3048-3064;
R. T. Baker, J. C. Gordon, C. W. Hamilton, N. J. Henson, P.-H. Lin, S. Maguire, M. Murugesu, B. L. Scott, N. C. Smythe, J. Am. Chem. Soc. 2012, 134, 5598-5609;
G. M. Adams, A. L. Colebatch, J. T. Skornia, A. I. McKay, H. C. Johnson, G. LloydJones, S. A. Macgregor, N. A. Beattie, A. S. Weller, J. Am. Chem. Soc. 2018, 140, 1481-1495; For reviews, see:
A. Rossin, M. Peruzzini, Chem. Rev. 2016, 116, 8848-8872;
A. L. Colebatch, A. S. Weller, Chem. Eur. J. 2019, 25, 1379-1390.
F. H. Stephens, V. Pons, R. T. Baker, Dalton Trans. 2007, 2613-2626;
T. B. Marder, Angew. Chem. Int. Ed. 2007, 46, 8116-8118;
Angew. Chem. 2007, 119, 8262-8264.
G. Chen, L. N. Zakharov, M. E. Bowden, A. J. Karkamkar, S. M. Whittemore, E. B. Garner, T. C. Mikulas, D. A. Dixon, T. Autrey, S.-Y. Liu, J. Am. Chem. Soc. 2015, 137, 134-137;
W. Luo, P. G. Campbell, L. N. Zakharov, S.-Y. Liu, J. Am. Chem. Soc. 2011, 133, 19326-19329;
A. Staubitz, M. Besora, N. J. Harvey, I. Manners, Inorg. Chem. 2008, 47, 5910-5918.
A. Ledoux, P. Larini, C. Boisson, V. Monteil, J. Raynaud, E. Lacôte, Angew. Chem. Int. Ed. 2015, 54, 15744-15749;
Angew. Chem. 2015, 127, 15970-15975; For an application of the dehydrogenated polymers, see:
T. Lorenz, M. Crumbach, T. Eckert, A. Lik, H. Helten, Angew. Chem. Int. Ed. 2017, 56, 2780-2784;
Angew. Chem. 2017, 129, 2824-2828.
We unsuccessfully attempted the direct free-radical polymerization of the amine-borane substituted styrene. We believe this failure is due to simultaneous dehydrogenation and/or early termination due to H-atom transfer from the monomer. For chain-substituted boron polymers with other properties, see:
K. Parab, K. Venkatasubbaiah, F. Jäkle, J. Am. Chem. Soc. 2006, 128, 12879-12885;
H. Kuhtz, F. Cheng, S. Schwedler, L. Böhling, A. Brockhinke, L. Weber, K. Parab, F. Jäkle, ACS Macro Lett. 2012, 1, 555-559;
K. Tanaka, K. Tamashima, A. Nagai, T. Okawa, Y. Chujo, Macromolecules 2013, 46, 2969-2975;
G. C. Welch, G. C. Bazan, J. Am. Chem. Soc. 2011, 133, 4632-4644;
Y. Kotsuchibashi, R. V. C. Agustin, J.-Y. Lu, D. G. Hall, R. Narain, ACS Macro Lett. 2013, 2, 260-264;
F. Cheng, E. M. Bonder, F. Jäkle, J. Am. Chem. Soc. 2013, 135, 17286-17289;
W. Wan, F. Cheng, F. Jäkle, Angew. Chem. Int. Ed. 2014, 53, 8934-8938;
Angew. Chem. 2014, 126, 9080-9084;
J. N. Cambre, D. Roy, S. R. Gondi, B. S. Sumerlin, J. Am. Chem. Soc. 2007, 129, 10348-10349.
M. Bowden, T. Autrey, Curr. Opin. Solid State Mater. Sci. 2011, 15, 73-79;
J. Li, S. M. Kathmann, H.-S. Hu, G. K. Schenter, T. Autrey, M. Gutowski, Inorg. Chem. 2010, 49, 7710-7720.
For use of other support materials, see:
A. Rossin, G. Tuci, L. Luconi, G. Giambastiani, ACS Catal. 2017, 7, 5035-5045 (MOFs);
J. Alipour, A. M. Shoushtari, A. Kaflou, J. Mater. Sci. 2015, 50, 3110-3117 (PMMA);
M. Rueda, L. M. Sanz-Moral, J. J. Segovia, A. Martin, Microporous Mesoporous Mater. 2017, 237, 189-200 (silica);
Z. Tang, X. Chen, H. Chen, L. Wu, X. Yu, Angew. Chem. Int. Ed. 2013, 52, 5832-5835;
Angew. Chem. 2013, 125, 5944-5947 (graphitic nano carbons);
S. Sepehri, A. Feaver, W. J. Shaw, C. J. Howard, Q. Zhang, T. Autrey, G. Cao, J. Phys. Chem. B 2007, 111, 14285-14289 (carbon cryogel).
For a similar observation, see: S. S. Mal, F. H. Stephens, R. T. Baker, Chem. Commun. 2011, 47, 2922-2924.
Pictures of the materials and of borazane before and after dehydrogenation can be found in the Supporting Information (see visuals). One can clearly see that, as opposed to our materials, borazane catastrophically expands by foaming upon thermal dehydrogenation.