Self-Assembling Behaviour of Perylene, Perylene Diimide, and Thionated Perylene Diimide Deciphered through Non-Covalent Interactions.
atoms in molecules
energy decomposition analysis
non-covalent interaction
perylene diimide derivatives
self-assembly
Journal
Chemphyschem : a European journal of chemical physics and physical chemistry
ISSN: 1439-7641
Titre abrégé: Chemphyschem
Pays: Germany
ID NLM: 100954211
Informations de publication
Date de publication:
05 12 2022
05 12 2022
Historique:
revised:
26
07
2022
received:
28
05
2022
pubmed:
27
7
2022
medline:
4
1
2023
entrez:
26
7
2022
Statut:
ppublish
Résumé
The π-conjugated supramolecular polymers (SMP) have gained vast popularity in materials chemistry and biomedicine due to their spectacular self-assembling behaviour. A detailed account of the electronic structure and bonding through quantum theory of atoms-in-molecules, non-covalent interactions, and energy decomposition analysis (EDA) in the oligomers of perylene, perylene diimide (PDI), and thionated-PDI (t-PDI) is presented. The oligomers of all three molecules show a slip angle of θ≈62° thus forming H-aggregates. The stacking pattern in perylene oligomers prefers a slip-stacked brick-layer order, while the bulkier PDI and t-PDI prefer a parallel step-wise pattern in their oligomers. Successive addition of monomers leads to a consequent rise in the association energy, although to a much greater extent in PDI and t-PDI than in perylene. While the major contribution to this association energy comes from the dispersion interactions in all three systems, the steric interactions in t-PDI quench the cooperativity in its SMP formation. A detailed analysis of the non-covalent interactions reveals the presence of π-π, π-hole⋅⋅⋅O=C, and π-hole⋅⋅⋅S=C electrostatic interactions playing a crucial role in the self-assembly process, which can be further implemented on developing force field-based methods for understanding the self-assembling mechanism in higher degree of oligomers.
Identifiants
pubmed: 35881033
doi: 10.1002/cphc.202200361
doi:
Substances chimiques
perylenediimide
0
Perylene
5QD5427UN7
Imides
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202200361Subventions
Organisme : SPARC, MHRD, Govt. of India
ID : SPARC/2018-2019/P1546/SL
Organisme : SPARC, MHRD, Govt. of India
ID : EMR/2015/001890
Organisme : SPARC, MHRD, Govt. of India
ID : SR/FST/CSII-026/2013
Organisme : CSIR, India
ID : 01(2987)/19/EMR-II
Organisme : Paramshakti supercomputing facility of IIT Kharagpur
Organisme : National Supercomputing Mission of the Government of India
Organisme : CDAC, Pune
Organisme : SPARC, MHRD
ID : SPARC/2018-2019/P1546/SL
Organisme : SPARC, MHRD
ID : EMR/2015/001890
Organisme : SPARC, MHRD
ID : SR/FST/CSII-026/2013
Informations de copyright
© 2022 Wiley-VCH GmbH.
Références
G. M. Whitesides, M. Boncheva, Proc. Natl. Acad. Sci. USA 2002, 99, 4769.
S. Rieth, C. Baddeley, J. D. Badjić, Soft Matter 2007, 3, 137.
D. Bialas, E. Kirchner, M. I. S. Röhr, F. Würthner, J. Am. Chem. Soc. 2021, 143, 4500.
F. Würthner, K. Meerholz, Chem. Eur. J. 2010, 16, 9366.
D. A. Uhlenheuer, K. Petkau, L. Brunsveld, Chem. Soc. Rev. 2010, 39, 2817.
C. Huang, S. Barlow, S. R. Marder, J. Org. Chem. 2011, 76, 2386.
F. Würthner, Chem. Commun. 2004, 1564-1579.
S. Chen, P. Slattum, C. Wang, L. Zang, Chem. Rev. 2015, 115, 11967.
T. Seki, X. Lin, S. Yagai, Asian J. Org. Chem. 2013, 2, 708.
Y. Guo, Z. Ma, X. Niu, W. Zhang, M. Tao, Q. Guo, Z. Wang, A. Xia, J. Am. Chem. Soc. 2019, 141, 12789.
N. Renaud, P. A. Sherratt, M. A. Ratner, J. Phys. Chem. Lett. 2013, 4, 1065.
Y. Geng, H.-B. Li, S.-X. Wu, Z.-M. Su, J. Mater. Chem. 2012, 22, 20840.
B. W. Chen, Y. W. Xu, L. Zhang, Appl. Mech. Mater. 2014, 513-517, 347.
F. Würthner, C. R. Saha-Möller, B. Fimmel, S. Ogi, P. Leowanawat, D. Schmidt, Chem. Rev. 2016, 116, 962.
T. Weil, T. Vosch, J. Hofkens, K. Peneva, K. Müllen, Angew. Chem. Int. Ed. 2010, 49, 9068.
F. Würthner, M. Stolte, Chem. Commun. 2011, 47, 5109.
J. Vura-Weis, M. A. Ratner, M. R. Wasielewski, J. Am. Chem. Soc. 2010, 132, 1738.
X. Zhan, A. Facchetti, S. Barlow, T. J. Marks, M. A. Ratner, M. R. Wasielewski, S. R. Marder, Adv. Mater. 2011, 23, 268.
M. Deutsch, S. Wirsing, D. Kaiser, R. F. Fink, P. Tegeder, B. Engels, J. Chem. Phys. 2020, 153, 224104.
C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 2002, 14, 99.
F. G. Brunetti, R. Kumar, F. Wudl, J. Mater. Chem. 2010, 20, 2934.
H. Langhals, J. Karolin, L. B.-A. Johansson, J. Chem. Soc. Faraday Trans. 1998, 94, 2919.
S. K. Lee, Y. Zu, A. Herrmann, Y. Geerts, K. Müllen, A. J. Bard, J. Am. Chem. Soc. 1999, 121, 3513.
G. Boobalan, P. K. M. Imran, C. Manoharan, S. Nagarajan, J. Colloid Interface Sci. 2013, 393, 377.
A. Nowak-Król, F. Würthner, Org. Chem. Front. 2019, 6, 1272.
Z. Chen, M. G. Debije, T. Debaerdemaeker, P. Osswald, F. Würthner, ChemPhysChem 2004, 5, 137.
H. Z. Chen, M. M. Ling, X. Mo, M. M. Shi, M. Wang, Z. Bao, Chem. Mater. 2007, 19, 816.
B. A. Jones, M. J. Ahrens, M.-H. Yoon, A. Facchetti, T. J. Marks, M. R. Wasielewski, Angew. Chem. Int. Ed. 2004, 43, 6363.
R. Schmidt, M. Ling, J. Oh, M. Winkler, M. Könemann, Z. Bao, F. Würthner, Adv. Mater. 2007, 19, 3692.
R. T. Weitz, K. Amsharov, U. Zschieschang, E. B. Villas, D. K. Goswami, M. Burghard, H. Dosch, M. Jansen, K. Kern, H. Klauk, J. Am. Chem. Soc. 2008, 130, 4637.
J. Rivnay, L. H. Jimison, J. E. Northrup, M. F. Toney, R. Noriega, S. Lu, T. J. Marks, A. Facchetti, A. Salleo, Nat. Mater. 2009, 8, 952.
F. Würthner, P. Osswald, R. Schmidt, T. E. Kaiser, H. Mansikkamäki, M. Könemann, Org. Lett. 2006, 8, 3765.
M. Gsänger, J. Oh, M. Könemann, H. Höffken, A.-M. Krause, Z. Bao, F. Würthner, Angew. Chem. Int. Ed. 2010, 49, 740.
L. Ma, Y. Guo, Y. Wen, Y. Liu, X. Zhan, Appl. Phys. Lett. 2013, 103, 203303.
A. J. Tilley, C. Guo, M. B. Miltenburg, T. B. Schon, H. Yan, Y. Li, D. S. Seferos, Adv. Funct. Mater. 2015, 25, 3321.
A. J. Tilley, R. D. Pensack, T. S. Lee, B. Djukic, G. D. Scholes, D. S. Seferos, J. Phys. Chem. C 2014, 118, 9996.
Y.-A. Duan, H.-B. Li, Y. Geng, Y. Wu, G.-Y. Wang, Z.-M. Su, Org. Electron. 2014, 15, 602.
N. Pearce, E. S. Davies, W. Lewis, N. R. Champness, ACS Omega 2018, 3, 14236.
L. M. Kozycz, C. Guo, J. G. Manion, A. J. Tilley, A. J. Lough, Y. Li, D. S. Seferos, J. Mater. Chem. C 2015, 3, 11505.
H. E. Symons, M. J. L. Hagemann, R. L. Harniman, C. F. J. Faul, J. Mater. Chem. C 2022, 10, 2828.
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.
C. Kulkarni, S. Balasubramanian, S. J. George, ChemPhysChem 2013, 14, 661.
J. Cornil, D. Beljonne, J.-P. Calbert, J.-L. Brédas, Adv. Mater. 2001, 13, 1053.
M. Wehner, F. Würthner, Nat. Rev. Chem. 2020, 4, 38.
L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071.
T. F. A. de Greef, E. W. Meijer, Nature 2008, 453, 171.
G. M. Whitesides, B. Grzybowski, Science 2002, 295, 2418.
H.-M. Zhao, J. Pfister, V. Settels, M. Renz, M. Kaupp, V. C. Dehm, F. Wu“rthner, R. F. Fink, B. Engels, J. Am. Chem. Soc. 2009, 131, 15660.
M. C. R. Delgado, E.-G. Kim, D. A. da Silva Filho, J.-L. Bredas, J. Am. Chem. Soc. 2010, 132, 3375.
C. M. Mauck, R. M. Young, M. R. Wasielewski, J. Phys. Chem. A 2017, 121, 784.
R. E. Cook, B. T. Phelan, R. J. Kamire, M. B. Majewski, R. M. Young, M. R. Wasielewski, J. Phys. Chem. A 2017, 121, 1607.
P. R. Horn, E. J. Sundstrom, T. A. Baker, M. Head-Gordon, J. Chem. Phys. 2013, 138, 134119.
R. J. Lindquist, K. M. Lefler, K. E. Brown, S. M. Dyar, E. A. Margulies, R. M. Young, M. R. Wasielewski, J. Am. Chem. Soc. 2014, 136, 14912.
K. E. Brown, W. A. Salamant, L. E. Shoer, R. M. Young, M. R. Wasielewski, J. Phys. Chem. Lett. 2014, 5, 2588.
R. F. Fink, J. Seibt, V. Engel, M. Renz, M. Kaupp, S. Lochbrunner, H. M. Zhao, J. Pfister, F. Würthner, B. Engels, J. Am. Chem. Soc. 2008, 130, 12858.
F. Gao, Y. Zhao, W. Liang, J. Phys. Chem. B. 2011, 115, 2699.
R. Z. Khaliullin, E. A. Cobar, R. C. Lochan, A. T. Bell, M. Head-Gordon, J. Phys. Chem. A 2007, 111, 8753.
J. Sung, A. Nowak-Król, F. Schlosser, B. Fimmel, W. Kim, D. Kim, F. Würthner, J. Am. Chem. Soc. 2016, 138, 9029.
C. Kaufmann, D. Bialas, M. Stolte, F. Würthner, J. Am. Chem. Soc. 2018, 140, 9986.
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.
Y. Hong, J. Kim, W. Kim, C. Kaufmann, H. Kim, F. Würthner, D. Kim, J. Am. Chem. Soc. 2020, 142, 7845.
H. J. Bohórquez, R. J. Boyd, C. F. Matta, J. Phys. Chem. A 2011, 115, 12991.
R. F. W. Bader, Acc. Chem. Res. 1985, 18, 9.
R. F. W. Bader, Chem. Rev. 1991, 91, 893.
S. J. Grabowski, J. Phys. Chem. A 2012, 116, 1838.
R. G. A. Bone, R. F. W. Bader, J. Phys. Chem. 1996, 100, 10892.
R. F. W. Bader, J. Phys. Chem. A 2009, 113, 10391.
R. F. W. Bader, J. Phys. Chem. A 2010, 114, 7431.
R. F. W. Bader, H. Essén, J. Chem. Phys. 1984, 80, 1943.
R. F. W. Bader, Atoms in Molecules: A Quantum Theory.International Series of Monographs on Chemistry 22, Oxford Science Publications 1990.
J. S. Murray, P. Lane, T. Clark, K. E. Riley, P. Politzer, J. Mol. Model. 2012, 18, 541.
H. Wang, W. Wang, W. J. Jin, Chem. Rev. 2016, 116, 5072.
E. R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras-García, A. J. Cohen, W. Yang, J. Am. Chem. Soc. 2010, 132, 6498.
W. Liang, M. Head-Gordon, J. Chem. Phys. 2004, 120, 10379.
E. A. Cobar, R. Z. Khaliullin, R. G. Bergman, M. Head-Gordon, Proc. Natl. Acad. Sci. USA 2007, 104, 6963.
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian∼16 Revision C.01 2016, gaussian Inc. Wallingford CT.
T. Lu, F. Chen, J. Comput. Chem. 2012, 33, 580.
W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graphics Modell. 1996, 14, 27.
P. Hohenberg, W. Kohn, Phys. Rev. 1964, 136, B864.
A. Zupan, K. Burke, M. Ernzerhof, J. P. Perdew, J. Chem. Phys. 1997, 106, 10184.
K. Kitaura, K. Morokuma, Int. J. Quantum Chem. 1976, 10, 325.
T. Ziegler, A. Rauk, Theor. Chim. Acta 1977, 46, 1.
J. P. Wagner, P. R. Schreiner, Angew. Chem. Int. Ed. 2015, 54, 12274.
G. Klebe, F. Graser, E. Hädicke, J. Berndt, Acta Crystallogr. Sect. B 1989, 45, 69.
A. Camerman, J. Trotter, J. M. Robertson, Proc. Roy. Soc. A 1964, 279, 129.
A. Sugie, W. Han, N. Shioya, T. Hasegawa, H. Yoshida, J. Phys. Chem. C 2020, 124, 9765.
A. Bauzá, T. J. Mooibroek, A. Frontera, ChemPhysChem 2015, 16, 2496.
D. Casanova, Int. J. Quantum Chem. 2015, 115, 442.
V. Settels, W. Liu, J. Pflaum, R. F. Fink, B. Engels, J. Comput. Chem. 2012, 33, 1544.
T. Zykova-Timan, P. Raiteri, M. Parrinello, J. Phys. Chem. B 2008, 112, 13231.
M. Kasha, Radiat. Res. 2012, 178, AV27.
N. J. Hestand, F. C. Spano, Chem. Rev. 2018, 118, 7069.
R. S. Wilson-Kovacs, X. Fang, M. J. L. Hagemann, H. E. Symons, C. F. J. Faul, Chem. Eur. J. 2022, 28, e202103443.
E. Kozma, M. Catellani, Dyes Pigm. 2013, 98, 160.
R. K. Gupta, A. A. Sudhakar, Langmuir 2019, 35, 2455.
A. E. Clark, C. Qin, A. D. Q. Li, J. Am. Chem. Soc. 2007, 129, 7586.
I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules (Second Edition), Academic Press, second edition edition 1971.
C.-Q. Wan, X.-D. Chen, T. C. W. Mak, CrystEngComm 2008, 10, 475.