Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch

Fenske MT, Meyer-Zaika W, Korth H-G, Vieker H, Turchanin A, Schmuck C (2013)
Journal of the American Chemical Society 135(22): 8342-8349.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Fenske, M. Tassilo; Meyer-Zaika, Wolfgang; Korth, Hans-Gert; Vieker, HenningUniBi; Turchanin, AndreyUniBi; Schmuck, Carsten
Abstract / Bemerkung
Derivatives of the self-complementary 2-guanidiniocarbonyl 5-carboxylate zwitterion (1) (previously reported by us to dimerize to 1.1 with an aggregation constant of ca. >10(10) M-1 in DMSO) aggregate in a diverse manner depending on, e.g., variation of concentration or its protonation state. The mode of aggregation was analyzed by spectroscopic (NMR, UV) and microscopic (AFM, SEM, HIM, and TEM) methods. Aggregation of dimers of these zwitterions to higher supramolecular structures was achieved by introduction of sec-amide substitutents at the 3-position, i.e., at the reward periphery of the parent binding motif. A butyl amide substituent as in 2b enables the discoid dimers to further aggregate into one-dimensional (rod-like) stacks. Quantitative UV dilution studies showed that this aggregation is strongly cooperative following a nucleation elongation mechanism. The amide hydrogen seems to be essential for this rod-like aggregation, as neither 1 nor a corresponding tert-amide congener 2a form comparable structures. Therefore, a hydrogen bond-assisted pi-pi interaction of the dimeric zwitterions is suggested to promote this aggregation mode, which is further affected by the nature of the amide substitutent (e.g., steric demand), enabling the formation of bundles of strands or even two-dimensional sheets. By exploiting the zwitterionic nature of the aggregating discoid dimers, a reversible pH switch was realized: dimerization of all compounds is suppressed by protonation of the carboxylate moiety, converting the zwitterions into typical cationic amphiphiles. Accordingly, typical nanostructures like vesicles, tubes, and flat sheets are formed reverisbly under acidic conditions, which reassemble into the original rod-like aggregates upon readjustment to neutral pH.
Erscheinungsjahr
2013
Zeitschriftentitel
Journal of the American Chemical Society
Band
135
Ausgabe
22
Seite(n)
8342-8349
ISSN
0002-7863
eISSN
1520-5126
Page URI
https://pub.uni-bielefeld.de/record/2612830

Zitieren

Fenske MT, Meyer-Zaika W, Korth H-G, Vieker H, Turchanin A, Schmuck C. Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch. Journal of the American Chemical Society. 2013;135(22):8342-8349.
Fenske, M. T., Meyer-Zaika, W., Korth, H. - G., Vieker, H., Turchanin, A., & Schmuck, C. (2013). Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch. Journal of the American Chemical Society, 135(22), 8342-8349. doi:10.1021/ja4025148
Fenske, M. Tassilo, Meyer-Zaika, Wolfgang, Korth, Hans-Gert, Vieker, Henning, Turchanin, Andrey, and Schmuck, Carsten. 2013. “Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch”. Journal of the American Chemical Society 135 (22): 8342-8349.
Fenske, M. T., Meyer-Zaika, W., Korth, H. - G., Vieker, H., Turchanin, A., and Schmuck, C. (2013). Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch. Journal of the American Chemical Society 135, 8342-8349.
Fenske, M.T., et al., 2013. Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch. Journal of the American Chemical Society, 135(22), p 8342-8349.
M.T. Fenske, et al., “Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch”, Journal of the American Chemical Society, vol. 135, 2013, pp. 8342-8349.
Fenske, M.T., Meyer-Zaika, W., Korth, H.-G., Vieker, H., Turchanin, A., Schmuck, C.: Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch. Journal of the American Chemical Society. 135, 8342-8349 (2013).
Fenske, M. Tassilo, Meyer-Zaika, Wolfgang, Korth, Hans-Gert, Vieker, Henning, Turchanin, Andrey, and Schmuck, Carsten. “Cooperative Self-Assembly of Discoid Dimers: Hierarchical Formation of Nanostructures with a pH Switch”. Journal of the American Chemical Society 135.22 (2013): 8342-8349.

16 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Hierarchical self-assembly of zwitterionic dendrimer-anionic surfactant complexes into multiple stimuli-responsive dynamic nanotubes.
Eghtesadi SA, Kashfipour MA, Sun X, Zhang W, Lillard RS, Cheng SZD, Liu T., Nanoscale 10(3), 2018
PMID: 29302659
Formation of Twisted β-Sheet Tapes from a Self-Complementary Peptide Based on Novel Pillararene-GCP Host-Guest Interaction with Gene Transfection Properties.
Hu XY, Ehlers M, Wang T, Zellermann E, Mosel S, Jiang H, Ostwaldt JE, Knauer SK, Wang L, Schmuck C., Chemistry 24(39), 2018
PMID: 29770977
Supramolecular Polymerization from Controllable Fabrication to Living Polymerization.
Huang Z, Qin B, Chen L, Xu JF, Faul CFJ, Zhang X., Macromol Rapid Commun 38(17), 2017
PMID: 28752583
Cooperative Supramolecular Polymerization of Fluorescent Platinum Acetylides for Optical Waveguide Applications.
Wang X, Han Y, Liu Y, Zou G, Gao Z, Wang F., Angew Chem Int Ed Engl 56(41), 2017
PMID: 28799686
Acid/Base-mediated uptake and release of halide anions with a preorganized aryl-triazole foldamer.
Zhao W, Wang Y, Shang J, Che Y, Jiang H., Chemistry 21(21), 2015
PMID: 25827450
Controlling aqueous self-assembly mechanisms by hydrophobic interactions.
Rudolph T, Kumar Allampally N, Fernández G, Schacher FH., Chemistry 20(43), 2014
PMID: 25201355
Manipulating assembly of cationic dipeptides using sulfonic azobenzenes.
Ma H, Fei J, Cui Y, Zhao J, Wang A, Li J., Chem Commun (Camb) 49(85), 2013
PMID: 24036697

References

Daten bereitgestellt von Europe PubMed Central.

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 23675908
PubMed | Europe PMC

Suchen in

Google Scholar