donor-acceptor foldamer; ion mobility; infrared spectroscopy; mass spectrometry; supramolecular chemistry
Abstract :
[en] The digital revolution sets a milestone in the progressive miniaturization of working devices and in the underlying advent of molecular machines. Foldamers involving mechanically entangled components with modular secondary structures are among the most promising designs for molecular switch-based applications. Characterizing the nature and dynamics of their intramolecular network following the application of a stimulus is the key to their performance. Here, we use non-dissociative electron transfers as a reductive stimulus in the gas phase and probe the consecutive co-conformational transitions of a donor-acceptor oligorotaxane foldamer using electrospray mass spectrometry interfaced with ion mobility and infrared ion spectroscopy. The comparison of collision cross section distributions for analogous closed-shell and radical molecular ions sheds light on their respective formation energetics while variations in their respective infrared absorption bands evidence different intramolecular organizations as the foldamer gets compact. These differences are compatible with the advent of radical-pairing interactions.
Research center :
MolSys - Molecular Systems - ULiège
Disciplines :
Chemistry
Author, co-author :
Hanozin, Emeline ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique
Mignolet, Benoît ; Université de Liège - ULiège > Département de chimie (sciences) > Laboratoire de chimie physique théorique
Martens, Jonathan
Berden, Giel
Sluysmans, Damien ; Université de Liège - ULiège > Département de chimie (sciences) > Nanochimie et systèmes moléculaires
Duwez, Anne-Sophie ; Université de Liège - ULiège > Département de chimie (sciences) > Nanochimie et systèmes moléculaires
Stoddart, Fraser
Eppe, Gauthier ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique
Oomens, Jos
De Pauw, Edwin ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique
Morsa, Denis ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique
Language :
English
Title :
Radical-Pairing Interactions in a Molecular Switch Evidenced by Ion Mobility Spectrometry and Infrared Ion Spectroscopy
B. L. Feringa, Angew. Chem. Int. Ed. 2017, 56, 11060–11078;
Angew. Chem. 2017, 129, 11206–11226.
V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3348–3391;
Angew. Chem. 2000, 112, 3484–3530.
S. Erbas-Cakmak, D. A. Leigh, C. T. McTernan, A. L. Nussbaumer, Chem. Rev. 2015, 115, 10081–10206.
W. R. Browne, B. L. Feringa, Nat. Nanotechnol. 2006, 1, 25–35.
E. R. Kay, D. A. Leigh, Angew. Chem. Int. Ed. 2015, 54, 10080–10088;
Angew. Chem. 2015, 127, 10218–10226.
P. L. Anelli, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1991, 113, 5131–5133.
I. Willner, B. Basnar, B. Willner, Adv. Funct. Mater. 2007, 17, 702–717.
E. Moulin, L. Faour, C. C. Carmona-Vargas, N. Giuseppone, Adv. Mater. 2020, 32, 1906036
C. J. Bruns, J. F. Stoddart, Adv. Polym. Sci. 2013, 261, 271–294.
S. Basu, A. Coskun, D. C. Friedman, M. A. Olson, D. Benítez, E. Tkatchouk, G. Barin, J. Yang, A. C. Fahrenbach, W. A. Goddard III, J. F. Stoddart, Chem. Eur. J. 2011, 17, 2107–2119.
I. Franco, G. C. Schatz, M. A. Ratner, J. Chem. Phys. 2009, 131, 124902.
Z. Zhu, C. J. Bruns, H. Li, J. Lei, C. Ke, Z. Liu, S. Shafaie, H. M. Colquhoun, J. F. Stoddart, Chem. Sci. 2013, 4, 1470–1483.
E. Hanozin, B. Mignolet, D. Morsa, D. Sluysmans, A.-S. Duwez, J. F. Stoddart, F. Remacle, E. De Pauw, ACS Nano 2017, 11, 10253–10263.
D. Sluysmans, F. Devaux, C. J. Bruns, J. F. Stoddart, A.-S. Duwez, Proc. Natl. Acad. Sci. U.S.A. 2018, 115, 9362–9366.
D. Sluysmans, S. Hubert, C. J. Bruns, Z. Zhu, J. F. Stoddart, A.-S. Duwez, Nat. Nanotechnol. 2018, 13, 209–214.
Y. Joo, V. Agarkar, S. H. Sung, B. M. Savoie, B. W. Boudouris, Science 2018, 359, 1391–1395.
A. Aviram, C. Joachim, M. Pomerantz, Chem. Phys. Lett. 1988, 146, 490–495.
Y. Wang, M. Frasconi, W. G. Liu, Z. Liu, A. A. Sarjeant, M. S. Nassar, Y. Y. Botros, W. A. Goddard III, J. F. Stoddart, J. Am. Chem. Soc. 2015, 137, 876–885.
A. Trabolsi, N. Khashab, A. C. Fahrenbach, D. C. Friedman, M. T. Colvin, K. K. Cotí, D. Benítez, E. Tkatchouk, J.-C. Olsen, M. E. Belowich, R. Carmielli, H. A. Khatib, W. A. Goddard III, M. R. Wasielewski, J. F. Stoddart, Nat. Chem. 2010, 2, 42–49.
A. Trabolsi, A. C. Fahrenbach, S. K. Dey, A. I. Share, D. C. Friedman, S. Basu, T. B. Gasa, N. M. Khashab, S. Saha, I. Aprahamian, H. A. Khatib, A. H. Flood, J. F. Stoddart, Chem. Commun. 2010, 46, 871–873.
A. C. Fahrenbach, J. C. Barnes, D. A. Lanfranchi, H. Li, A. Coskun, J. J. Gassensmith, Z. Liu, D. Benítez, A. Trabolsi, W. A. Goddard III, M. Elhabiri, J. F. Stoddart, J. Am. Chem. Soc. 2012, 134, 3061–3072.
J. E. P. Syka, J. J. Coon, M. J. Schroeder, J. Shabanowitz, D. F. Hunt, Proc. Natl. Acad. Sci. USA 2004, 101, 9528–9533.
C. Gütz, R. Hovorka, N. Struch, J. Bunzen, G. Meyer-Eppler, Z. W. Qu, S. Grimme, F. Topić, K. Rissanen, M. Cetina, M. Engeser, A. Lützen, J. Am. Chem. Soc. 2014, 136, 11830–11838.
M. A. Kaczorowska, H. J. Cooper, J. Am. Soc. Mass Spectrom. 2009, 20, 674–681.
R. Hovorka, M. Engeser, A. Lützen, Int. J. Mass Spectrom. 2013, 354–355, 152–158.
M. A. Kaczorowska, A. C. G. Hotze, M. J. Hannon, H. J. Cooper, J. Am. Soc. Mass Spectrom. 2010, 21, 300–309.
M. U. Munshi, S. M. Craig, G. Berden, J. Martens, A. F. Deblase, D. J. Foreman, S. A. McLuckey, J. Oomens, M. A. Johnson, J. Phys. Chem. Lett. 2017, 8, 5047–5052.
H. P. Gunawardena, M. He, P. A. Chrisman, S. J. Pitteri, J. M. Hogan, B. D. M. Hodges, S. A. McLuckey, J. Am. Chem. Soc. 2005, 127, 12627–12639.
D. L. Marshall, B. L. J. Poad, E. T. Luis, R. A. Da Silva Rodrigues, S. J. Blanksby, K. M. Mullen, Chem. Commun. 2020, 56, 13575–13578.
V. Gabelica, E. Marklund, Curr. Opin. Chem. Biol. 2018, 42, 51–59.
J. Martens, J. Grzetic, G. Berden, J. Oomens, Nat. Commun. 2016, 7, 11754.
J. B. Fenn, M. Mann, C. K. Meng, S. F. Wong, C. M. Whitehouse, Science 1989, 246, 64–71.
J. J. Coon, J. E. P. Syka, J. C. Schwartz, J. Shabanowitz, D. F. Hunt, Int. J. Mass Spectrom. 2004, 236, 33–42.
T. Wyttenbach, C. Bleiholder, M. T. Bowers, Anal. Chem. 2013, 85, 2191–2199.
J. J. P. Stewart, J. Mol. Model. 2007, 13, 1173–1213.
D. E. Clemmer, D. H. Russell, E. R. Williams, Acc. Chem. Res. 2017, 50, 556–560.
K. Breuker, F. W. Mclafferty, Proc. Natl. Acad. Sci. USA 2008, 105, 18145–18152.
F. Tureček, R. R. Julian, Chem. Rev. 2013, 113, 6691–6733.
A. Barth, Biochim. Biophys. Acta Bioenerg. 2007, 1767, 1073–1101.
M. B. Nielsen, Z.-T. Li, J. Becher, J. Mater. Chem. 1997, 7, 1175–1187.
A. I. González Flórez, E. Mucha, D. S. Ahn, S. Gewinner, W. Schöllkopf, K. Pagel, G. Von Helden, Angew. Chem. Int. Ed. 2016, 55, 3295–3299;
Angew. Chem. 2016, 128, 3356–3360.
Y. Wang, M. Frasconi, W.-G. Liu, J. Sun, Y. Wu, M. S. Nassar, Y. Y. Botros, W. A. Goddard III, M. R. Wasielewski, J. F. Stoddart, ACS Cent. Sci. 2016, 2, 89–98.
M. Datta, R. E. Jansson, J. J. Freeman, Appl. Spectrosc. 1986, 40, 251–258.
J. M. Klein, H. Squire, W. Dean, B. E. Gurkan, J. Phys. Chem. B 2020, 124, 6348–6357.
M. Ito, H. Sasaki, M. Takahashi, J. Phys. Chem. 1987, 91, 3932–3934.
E. E. Ferguson, F. A. Matsen, J. Chem. Phys. 1958, 29, 105–107.
Y. Zhao, D. G. Truhlar, Theor. Chem. Acc. 2008, 120, 215–241.
E. Katz, L. Sheeney-Haj-Ichia, I. Willner, Angew. Chem. Int. Ed. 2004, 43, 3292–3300;
Angew. Chem. 2004, 116, 3354–3362.
N. Elgrishi, K. J. Rountree, B. D. McCarthy, E. S. Rountree, T. T. Eisenhart, J. L. Dempsey, J. Chem. Educ. 2018, 95, 197–206.
W. Kaim, J. Fiedler, Chem. Soc. Rev. 2009, 38, 3373–3382.
B. Helmich-Paris, J. Chem. Phys. 2019, 150, 174121.
J. W. Park, R. Al-Saadon, M. K. Macleod, T. Shiozaki, B. Vlaisavljevich, Chem. Rev. 2020, 120, 5878–5909.
H. V. Schröder, A. Mekic, H. Hupatz, S. Sobottka, F. Witte, L. H. Urner, M. Gaedke, K. Pagel, B. Sarkar, B. Paulus, C. A. Schalley, Nanoscale 2018, 10, 21425–21433.
H. V. Schröder, J. M. Wollschläger, C. A. Schalley, Chem. Commun. 2017, 53, 9218–9221.
T. M. Hedison, S. Hay, N. S. Scrutton, Nitric Oxide 2017, 63, 61–67.
H. L. Rutledge, F. A. Tezcan, Chem. Rev. 2020, 120, 5158–5193.