A Molecular Strategy to Lock-in the Conformation of a Perylene Bisimide-Derived Supramolecular Polymer.
electrochemistry
excitonic properties
perylene bisimide
semiconducting nanomaterials
supramolecular polymer
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:
04 May 2020
04 May 2020
Historique:
received:
14
09
2019
revised:
21
12
2019
pubmed:
28
1
2020
medline:
28
1
2020
entrez:
28
1
2020
Statut:
ppublish
Résumé
Locking-in the conformation of supramolecular assemblies provides a new avenue to regulate the (opto)electronic properties of robust nanoscale objects. In the present contribution, we show that the covalent tethering of a perylene bisimide (PBI)-derived supramolecular polymer with a molecular locker enables the formation of a locked superstructure equipped with emergent structure-function relationships. Experiments that exploit variable-temperature ground-state electronic absorption spectroscopy unambiguously demonstrate that the excitonic coupling between nearest neighboring units in the tethered superstructure is preserved at a temperature (371 K) where the pristine, non-covalent assembly exists exclusively in a molecularly dissolved state. A close examination of the solid-state morphologies reveals that the locked superstructure engenders the formation of hierarchical 1D materials which are not achievable by unlocked assemblies. To complement these structural attributes, we further demonstrate that covalently tethering a supramolecular polymer built from PBI subunits enables the emergence of electronic properties not evidenced in non-covalent assemblies. Using cyclic voltammetry experiments, the elucidation of the potentiometric properties of the locked superstructure reveals a 100-mV stabilization of the conduction band energy when compared to that recorded for the non-covalent assembly.
Identifiants
pubmed: 31984605
doi: 10.1002/anie.201911780
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
7487-7493Subventions
Organisme : The Arnold and Mabel Beckman Foundation
ID : BYI2018
Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
P. P. Ghoroghchian, P. R. Frail, K. Susumu, D. Blessington, A. K. Brannan, F. S. Bates, B. Chance, D. A. Hammer, M. J. Therien, Proc. Natl. Acad. Sci. USA 2005, 102, 2922-2927.
J.-H. Olivier, J. Park, P. Deria, J. Rawson, Y. Bai, S. A. Kumbhar, J. M. Therien, Angew. Chem. Int. Ed. 2015, 54, 8133-8138;
Angew. Chem. 2015, 127, 8251-8256;
T. M. Wilson, T. A. Zeidan, M. Hariharan, F. D. Lewis, M. R. Wasielewski, Angew. Chem. Int. Ed. 2010, 49, 2385-2388;
Angew. Chem. 2010, 122, 2435-2438;
M. R. Wasielewski, Acc. Chem. Res. 2009, 42, 1910-1921;
M. Ortiz, S. Cho, J. Niklas, S. Kim, O. G. Poluektov, W. Zhang, G. Rumbles, J. Park, J. Am. Chem. Soc. 2017, 139, 4286-4289;
M. Krzeszewski, E. M. Espinoza, C. Červinka, J. B. Derr, J. A. Clark, D. Borchardt, G. J. O. Beran, D. T. Gryko, V. I. Vullev, Angew. Chem. Int. Ed. 2018, 57, 12365-12369;
Angew. Chem. 2018, 130, 12545-12549.
A. Kunzmann, M. Gruber, R. Casillas, J. Zirzlmeier, M. Stanzel, W. Peukert, R. R. Tykwinski, D. M. Guldi, Angew. Chem. Int. Ed. 2018, 57, 10742-10747;
Angew. Chem. 2018, 130, 10902-10907;
A. K. Le, J. A. Bender, D. H. Arias, D. E. Cotton, J. C. Johnson, S. T. Roberts, J. Am. Chem. Soc. 2018, 140, 814-826;
A. K. Le, J. A. Bender, S. T. Roberts, J. Phys. Chem. Lett. 2016, 7, 4922-4928.
P. C. Mondal, N. Kantor-Uriel, S. P. Mathew, F. Tassinari, C. Fontanesi, R. Naaman, Adv. Mater. 2015, 27, 1924-1927;
B. Göhler, V. Hamelbeck, T. Z. Markus, M. Kettner, G. F. Hanne, Z. Vager, R. Naaman, H. Zacharias, Science 2011, 331, 894-897.
S. R. Diegelmann, J. M. Gorham, J. D. Tovar, J. Am. Chem. Soc. 2008, 130, 13840-13841;
S. S. Panda, H. E. Katz, J. D. Tovar, Chem. Soc. Rev. 2018, 47, 3640-3658;
V. Faramarzi, F. Niess, E. Moulin, M. Maaloum, J.-F. Dayen, J.-B. Beaufrand, S. Zanettini, B. Doudin, N. Giuseppone, Nat. Chem. 2012, 4, 485;
O. A. Bell, G. Wu, J. S. Haataja, F. Brömmel, N. Fey, A. M. Seddon, R. L. Harniman, R. M. Richardson, O. Ikkala, X. Zhang, C. F. J. Faul, J. Am. Chem. Soc. 2015, 137, 14288-14294.
N. J. Hestand, F. C. Spano, Chem. Rev. 2018, 118, 7069-7163;
N. J. Hestand, F. C. Spano, Acc. Chem. Res. 2017, 50, 341-350;
N. J. Hestand, F. C. Spano, J. Chem. Phys. 2015, 143, 244707;
J. Vura-Weis, M. A. Ratner, M. R. Wasielewski, J. Am. Chem. Soc. 2010, 132, 1738-1739;
C. Kaufmann, D. Bialas, M. Stolte, F. Würthner, J. Am. Chem. Soc. 2018, 140, 9986-9995.
P. A. Korevaar, T. F. A. de Greef, E. W. Meijer, Chem. Mater. 2014, 26, 576-586;
T. F. A. De Greef, M. M. J. Smulders, M. Wolffs, A. P. H. J. Schenning, R. P. Sijbesma, E. W. Meijer, Chem. Rev. 2009, 109, 5687-5754.
R. van der Weegen, J. P. Teunissen Abraham, E. W. Meijer, Chem. Eur. J. 2017, 23, 3773-3783;
P. A. Korevaar, S. J. George, A. J. Markvoort, M. M. J. Smulders, P. A. J. Hilbers, A. P. H. J. Schenning, T. F. A. De Greef, E. W. Meijer, Nature 2012, 481, 492-497;
J. Leira-Iglesias, A. Sorrenti, A. Sato, P. A. Dunne, T. M. Hermans, Chem. Commun. 2016, 52, 9009-9012;
S. Ogi, K. Sugiyasu, S. Manna, S. Samitsu, M. Takeuchi, Nat. Chem. 2014, 6, 188;
S. Ogi, V. Stepanenko, K. Sugiyasu, M. Takeuchi, F. Würthner, J. Am. Chem. Soc. 2015, 137, 3300-3307;
T. Fukui, S. Kawai, S. Fujinuma, Y. Matsushita, T. Yasuda, T. Sakurai, S. Seki, M. Takeuchi, K. Sugiyasu, Nat. Chem. 2017, 9, 493-499;
T. Fukui, M. Takeuchi, K. Sugiyasu, Sci. Rep. 2017, 7, 2425;
C. Jarrett-Wilkins, X. He, H. E. Symons, R. L. Harniman, C. F. J. Faul, I. Manners, Chem. Eur. J. 2018, 24, 15556-15565;
A. Aliprandi, M. Mauro, L. De Cola, Nat. Chem. 2016, 8, 10.
H. Che, B. C. Buddingh, J. C. M. van Hest, Angew. Chem. Int. Ed. 2017, 56, 12581-12585;
Angew. Chem. 2017, 129, 12755-12759;
A. Sorrenti, J. Leira-Iglesias, A. J. Markvoort, T. F. A. de Greef, T. M. Hermans, Chem. Soc. Rev. 2017, 46, 5476-5490;
A. Sorrenti, J. Leira-Iglesias, A. Sato, T. M. Hermans, Nat. Commun. 2017, 8, 15899.
P. A. Rupar, G. Cambridge, M. A. Winnik, I. Manners, J. Am. Chem. Soc. 2011, 133, 16947-16957;
P. A. Rupar, L. Chabanne, M. A. Winnik, I. Manners, Science 2012, 337, 559;
X. Wang, K. Liu, A. C. Arsenault, D. A. Rider, G. A. Ozin, M. A. Winnik, I. Manners, J. Am. Chem. Soc. 2007, 129, 5630-5639.
J. Motoyanagi, T. Fukushima, N. Ishii, T. Aida, J. Am. Chem. Soc. 2006, 128, 4220-4221;
T. Yamamoto, T. Fukushima, A. Kosaka, W. Jin, Y. Yamamoto, N. Ishii, T. Aida, Angew. Chem. Int. Ed. 2008, 47, 1672-1675;
Angew. Chem. 2008, 120, 1696-1699.
S. M. Chin, C. V. Synatschke, S. Liu, R. J. Nap, N. A. Sather, Q. Wang, Z. Álvarez, A. N. Edelbrock, T. Fyrner, L. C. Palmer, I. Szleifer, M. Olvera de la Cruz, S. I. Stupp, Nat. Commun. 2018, 9, 2395;
K. Sato, W. Ji, L. C. Palmer, B. Weber, M. Barz, S. I. Stupp, J. Am. Chem. Soc. 2017, 139, 8995-9000;
M. Fernández-Castaño Romera, X. Lou, J. Schill, G. ter Huurne, P.-P. K. H. Fransen, I. K. Voets, C. Storm, R. P. Sijbesma, J. Am. Chem. Soc. 2018, 140, 17547-17555.
K. Liu, A. Levy, C. Liu, J.-H. Olivier, Chem. Mater. 2018, 30, 2143-2150;
K. Liu, A. Mukhopadhyay, A. Ashcraft, C. Liu, A. Levy, P. Blackwelder, J.-H. Olivier, Chem. Commun. 2019, 55, 5603-5606.
Z. Chen, V. Stepanenko, V. Dehm, P. Prins, L. D. A. Siebbeles, J. Seibt, P. Marquetand, V. Engel, F. Würthner, Chem. Eur. J. 2007, 13, 436-449;
G. L. Eakins, J. K. Gallaher, R. A. Keyzers, A. Falber, J. E. A. Webb, A. Laos, Y. Tidhar, H. Weissman, B. Rybtchinski, P. Thordarson, J. M. Hodgkiss, J. Phys. Chem. B 2014, 118, 8642-8651;
J. Seibt, P. Marquetand, V. Engel, Z. Chen, V. Dehm, F. Würthner, Chem. Phys. 2006, 328, 354-362.
F. C. Spano, C. Silva, Annu. Rev. Phys. Chem. 2014, 65, 477-500;
J. Clark, J.-F. Chang, F. C. Spano, R. H. Friend, C. Silva, Appl. Phys. Lett. 2009, 94, 163306.
B. Hammouda, D. L. Ho, S. Kline, Macromolecules 2004, 37, 6932-6937;
R. Kjellander, E. Florin, J. Chem. Soc. Faraday Trans. 1 1981, 77, 2053-2077;
K.-J. Liu, J. L. Parsons, Macromolecules 1969, 2, 529-533.
L. Martínez, M. Tello, M. Díaz, E. Román, R. Garcia, Y. Huttel, Rev. Sci. Instrum. 2011, 82, 023710;
Y. Gan, Surf. Sci. Rep. 2009, 64, 99-121.
R. Scott Lokey, B. L. Iverson, Nature 1995, 375, 303-305.
C. Liu, K. Liu, J. Klutke, A. Ashcraft, S. Steefel, J.-H. Olivier, J. Mater. Chem. C 2018, 6, 11980-11991;
P. Deria, J.-H. Olivier, J. Park, M. J. Therien, J. Am. Chem. Soc. 2014, 136, 14193-14199.
M. Mas-Torrent, C. Rovira, Chem. Rev. 2011, 111, 4833-4856;
V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J.-L. Brédas, Chem. Rev. 2007, 107, 926-952.
Y. Wu, M. Frasconi, D. M. Gardner, P. R. McGonigal, S. T. Schneebeli, M. R. Wasielewski, J. F. Stoddart, Angew. Chem. Int. Ed. 2014, 53, 9476-9481;
Angew. Chem. 2014, 126, 9630-9635;
A. Takai, T. Yasuda, T. Ishizuka, T. Kojima, M. Takeuchi, Angew. Chem. Int. Ed. 2013, 52, 9167-9171;
Angew. Chem. 2013, 125, 9337-9341.