Stabilization of High Oxidation State Upconversion Nanoparticles by N-Heterocyclic Carbenes
Nadja Möller
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
These authors contributed equally to this work.
Search for more papers by this authorAndreas Rühling
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
These authors contributed equally to this work.
Search for more papers by this authorSebastian Lamping
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
Search for more papers by this authorTim Hellwig
Westfälische Wilhelms-Universität Münster, Angewandte Physik, Corrensstrasse 2, 48149 Münster, Germany
Search for more papers by this authorProf. Dr. Carsten Fallnich
Westfälische Wilhelms-Universität Münster, Angewandte Physik, Corrensstrasse 2, 48149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Bart Jan Ravoo
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Frank Glorius
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
Search for more papers by this authorNadja Möller
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
These authors contributed equally to this work.
Search for more papers by this authorAndreas Rühling
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
These authors contributed equally to this work.
Search for more papers by this authorSebastian Lamping
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
Search for more papers by this authorTim Hellwig
Westfälische Wilhelms-Universität Münster, Angewandte Physik, Corrensstrasse 2, 48149 Münster, Germany
Search for more papers by this authorProf. Dr. Carsten Fallnich
Westfälische Wilhelms-Universität Münster, Angewandte Physik, Corrensstrasse 2, 48149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Bart Jan Ravoo
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
Search for more papers by this authorCorresponding Author
Prof. Dr. Frank Glorius
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 4, 8149 Münster, Germany
Search for more papers by this authorGraphical Abstract
Up, up, and carbene: High oxidation state NaYF4:Yb,Tm upconversion nanoparticles (UCNPs) were stabilized by N-heterocyclic carbenes (NHCs) through a ligand-exchange reaction from a well-defined precursor and characterized in detail. The ligands for such nanoparticles require different properties compared to elemental metal nanoparticles. This new photoactive material was employed in reactions of photoresponsive molecules.
Abstract
The stabilization of high oxidation state nanoparticles by N-heterocyclic carbenes is reported. Such nanoparticles represent an important subset in the field of nanoparticles, with different and more challenging requirements for suitable ligands compared to elemental metal nanoparticles. N-Heterocyclic carbene coated NaYF4:Yb,Tm upconversion nanoparticles were synthesized by a ligand-exchange reaction from a well-defined precursor. This new photoactive material was characterized in detail and employed in the activation of photoresponsive molecules by low-intensity near-infrared light (λ=980 nm).
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| anie201611506-sup-0001-misc_information.pdf6.1 MB | Supplementary |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1Selected examples for applications of nanoparticles:
- 1aC. Burda, X. Chen, R. Narayanan, M. A. El-Sayed, Chem. Rev. 2005, 105, 1025;
- 1bD. Astruc, F. Lu, J. R. Aranzaes, Angew. Chem. Int. Ed. 2005, 44, 7852; Angew. Chem. 2005, 117, 8062;
- 1cR. J. White, R. Luque, V. L. Budarin, J. H. Clark, D. J. Macquarrie, Chem. Soc. Rev. 2009, 38, 481;
- 1dL. D. Pachón, G. Rothenberg, Appl. Organomet. Chem. 2008, 22, 288;
- 1eR. V. Jagadeeshm, A.-E. Surkus, H. Junge, M.-M. Pohl, J. Radnik, J. Rabeah, H. Huan, V. Schünemann, A. Brückner, M. Beller, Science 2013, 342, 1073;
- 1fJ. H. Schenkel, A. Samanta, B. J. Ravoo, Adv. Mater. 2014, 26, 1076;
- 1gA. Samanta, B. J. Ravoo, Angew. Chem. Int. Ed. 2014, 53, 12946; Angew. Chem. 2014, 126, 13160;
- 1hG. Y. Tonga, Y. Jeong, B. Duncan, T. Mizuhara, R. Mout, R. Das, S. T. Kim, Y.-C. Yeh, B. Yan, S. Hou, V. M. Rotello, Nat. Chem. 2015, 7, 597.
- 2
- 2aB. L. Cushing, V. L. Kolesnichenko, C. J. O'Connor, Chem. Rev. 2004, 104, 3893;
- 2bL. S. Ott, R. G. Finke, Coord. Chem. Rev. 2007, 251, 1075.
- 3Selected Reviews on NHCs:
- 3aF. E. Hahn, M. C. Jahnke, Angew. Chem. Int. Ed. 2008, 47, 3122; Angew. Chem. 2008, 120, 3166;
- 3cS. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612;
- 3dT. Dröge, F. Glorius, Angew. Chem. Int. Ed. 2010, 49, 6940; Angew. Chem. 2010, 122, 7094;
- 3eM. N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 2014, 510, 485;
- 3fA. V. Zhukhovitskiy, M. J. MacLeod, J. A. Johnson, Chem. Rev. 2015, 115, 11503.
- 4Selected examples for NHCs as ligands for unsupported nanoparticles:
- 4aJ. Vignolle, T. D. Tilley, Chem. Commun. 2009, 7230;
- 4bE. C. Hurst, K. Wilson, I. J. S. Fairlamb, V. Chechik, New J. Chem. 2009, 33, 1837;
- 4cP. Lara, O. Rivada-Wheelaghan, S. Conejero, R. Poteau, K. Philippot, B. Chaudret, Angew. Chem. Int. Ed. 2011, 50, 12080; Angew. Chem. 2011, 123, 12286;
- 4dD. Gonzalez-Galvez, P. Lara, O. Rivada-Wheelaghan, S. Conejero, B. Chaudret, K. Philippot, P. W. N. M. van Leeuwen, Catal. Sci. Technol. 2013, 3, 99;
- 4eX. Ling, N. Schaeffer, S. Roland, M.-P. Pileni, Langmuir 2013, 29, 12647;
- 4fE. A. Baquero, S. Tricard, J. C. Flores, E. de Jesús, B. Chaudret, Angew. Chem. Int. Ed. 2014, 53, 13220; Angew. Chem. 2014, 126, 13436;
- 4gH.-X. Liu, X. He, L. Zhao, Chem. Commun. 2014, 50, 971;
- 4hM. Rodríguez-Castillo, D. Laurencin, F. Tielens, A. van der Lee, S. Clément, Y. Guari, S. Richeter, Dalton Trans. 2014, 43, 5978;
- 4iS. G. Song, C. Satheeshkumar, J. Park, J. Ahn, T. Premkumar, Y. Lee, C. Song, Macromolecules 2014, 47, 6566.
- 5Selected examples for NHCs as ligands for supported nanoparticles:
- 5aK. V. S. Ranganath, J. Kloesges, A. H. Schäfer, F. Glorius, Angew. Chem. Int. Ed. 2010, 49, 7786; Angew. Chem. 2010, 122, 7952;
- 5bD. Yu, M. X. Tan, Y. Zhang, Adv. Synth. Catal. 2012, 354, 969;
- 5cJ. B. Ernst, S. Muratsugu, F. Wang, M. Tada, F. Glorius, J. Am. Chem. Soc. 2016, 138, 10718.
- 6Selected examples for NHCs on metal surfaces:
- 6aA. V. Zhukhovitskiy, M. G. Mavros, T. V. Voorhis, J. A. Johnson, J. Am. Chem. Soc. 2013, 135, 7418;
- 6bC. M. Crudden, J. H. Horton, I. I. Ebralidze, O. V. Zenkina, A. B. McLean, B. Drevniok, Z. She, H.-B. Kraatz, N. J. Mosey, T. Seki, E. C. Keske, J. D. Leake, A. Rousina-Webb, G. Wu, Nat. Chem. 2014, 6, 409;
- 6cG. Wang, A. Rühling, S. Amirjalayer, M. Knor, J. B. Ernst, C. Richter, H.-J. Gao, A. Timmer, H.-Y. Gao, N. L. Doltsinis, F. Glorius, H. Fuchs, Nat. Chem. 2017, 9, 152.
- 7C. Richter, K. Schaepe, F. Glorius, B. J. Ravoo, Chem. Commun. 2014, 50, 3204.
- 8
- 8aL. S. Ott, M. L. Cline, M. Deetlefs, K. R. Seddon, R. G. Finke, J. Am. Chem. Soc. 2005, 127, 5758;
- 8bL. S. Ott, S. Campbell, K. R. Seddon, R. G. Finke, Inorg. Chem. 2007, 46, 10335;
- 8cJ. D. Scholten, G. Ebeling, J. Dupont, Dalton Trans. 2007, 5554;
- 8dJ. D. Scholten, J. Dupont, Organometallics 2008, 27, 4439;
- 8eY. E. Corilo, F. M. Nachtigall, P. V. Abdelnur, G. Ebeling, J. Dupont, M. N. Eberlin, RSC Adv. 2011, 1, 73.
- 9A. Ferry, K. Schaepe, P. Tegeder, C. Richter, K. M. Chepiga, B. J. Ravoo, F. Glorius, ACS Catal. 2015, 5, 5414.
- 10M. J. MacLeod, J. A. Johnson, J. Am. Chem. Soc. 2015, 137, 7974.
- 11A. Rühling, K. Schaepe, L. Rakers, B. Vonhören, P. Tegeder, B. J. Ravoo, F. Glorius, Angew. Chem. Int. Ed. 2016, 55, 5856; Angew. Chem. 2016, 128, 5950.
- 12NHCs have been used to stabilize nanoclusters by binding to oxidized metal centers:
- 12aJ. L. Durham, W. B. Wilson, D. N. Huh, R. McDonald, L. F. Szczepura, Chem. Commun. 2015, 51, 10536; NHC derivatives have been applied in stabilizing MgO nanoparticles:
- 12bM. Shaikh, M. Sahu, S. Khilari, A. K. Kumar, P. Maji, K. V. S. Ranganath, RSC Adv. 2016, 6, 82591;
- 12cM. Shaikh, M. Sahu, P. K. Gavel, G. R. Turpu, S. Khilari, D. Pradhan, K. V. S. Ranganath, Catal. Commun. 2016, 84, 89.
- 13P. Rahman, M. Green, Nanoscale 2009, 1, 214.
- 14
- 14aG. Chen, H. Qiu, P. N. Prasad, X. Chen, Chem. Rev. 2014, 114, 5161;
- 14bJ. Zhou, Q. Liu, W. Feng, Y. Sun, F. Li, Chem. Rev. 2015, 115, 395;
- 14cH. Dong, S.-R. Du, X.-Y. Zheng, G.-M. Lyu, L.-D. Sun, L.-D. Li, P.-Z. Zhang, C. Zhang, C.-H. Yan, Chem. Rev. 2015, 115, 10725.
- 15Selected examples on different applications of upconversion nanoparticles:
- 15aN. Bogdan, F. Vetrone, G. A. Ozin, J. A. Capobianco, Nano Lett. 2011, 11, 835;
- 15bB. F. Zhang, M. Frigoli, F. Angiuli, F. Vetrone, J. A. Capobianco, Chem. Commun. 2012, 48, 7244;
- 15cQ. Yu, E. M. Rodriguez, R. Naccache, P. Forgione, G. Lamoueux, F. Sanz-Rodriguez, D. Scheglmann, J. A. Capobianco, Chem. Commun. 2014, 50, 12150;
- 15dJ. Lai, Y. Zhang, N. Pasquale, K.-B. Lee, Angew. Chem. Int. Ed. 2014, 53, 14419; Angew. Chem. 2014, 126, 14647;
- 15eW. Li, Z. Chen, L. Zhou, Z. Li, J. Ren, X. Qu, J. Am. Chem. Soc. 2015, 137, 8199;
- 15fT. Wu, N. R. Branda, Chem. Commun. 2016, 52, 8636;
- 15gG. Jalani, R. Naccache, D. H. Rosenzweig, L. Haglund, F. Vetrone, M. Cerruti, J. Am. Chem. Soc. 2016, 138, 1078.
- 16J.-C. Boyer, F. Vetrone, L. A. Cuccia, J. A. Capobianco, J. Am. Chem. Soc. 2006, 128, 7444.
- 17P. L. Arnold, I. J. Casely, Chem. Rev. 2009, 109, 3599.
- 18H. Liu, C. T. Xu, G. Dumlupinar, O. B. Jensen, P. E. Andersen, S. Andersson-Engels, Nanoscale 2013, 5, 10034.
- 19
- 19aZ. Chen, W. Sun, H.-J. Butt, S. Wu, Chem. Eur. J. 2015, 21, 9165;
- 19bN. Möller, T. Hellwig, L. Stricker, S. Engel, C. Fallnich, B. J. Ravoo, Chem. Commun. 2017, 53, 240.
- 20
- 20aS. V. Wegner, O. I. Sentürk, J. P. Spatz, Sci. Rep. 2015, 5, 18309;
- 20bS. Wu, H.-J. Butt, Adv. Mater. 2016, 28, 1208;
- 20cB. Yan, J.-C. Boyer, D. Habault, N. R. Branda, Y. Zhao, J. Am. Chem. Soc. 2012, 134, 16558;
- 20dY. Yang, F. Liu, X. Liu, B. Xing, Nanoscale 2013, 5, 231;
- 20eS. Mura, J. Nicolas, P. Couvreur, Nat. Mater. 2013, 12, 991;
- 20fM. S. Kim, S. L. Diamond, Bioorg. Med. Chem. Lett. 2006, 16, 4007.
