Organic Letters
Letter
disassembled, the racemization of the sample takes place (inset
in Figure 2).
(c) Janke, R. H.; Haufe, G.; Wu
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To summarize, the results presented herein describe the
supramolecular polymerization and the noncovalent forces
operating in the self-assembly of 1,14-unsubstituted [5]-
helicenes. The studies presented in the manuscript demonstrate
that the enantiopurity of the sample changes the supra-
molecular polymerization mechanism that switches from an
isodesmic one, for the racemic mixture, to a cooperative one for
the enantioenriched M-2. More importantly, we demonstrate
that, due to the organized self-assembly of these unsubstituted
curved PAHs at the fjord region, they are conformationally
stable, thus demonstrating the enormous potential of supra-
molecular polymerization to accomplish configurational
stability of [5]helicenes.
(
8) Ravat, P.; Hinkelmann, R.; Steinebrunner, D.; Prescimone, A.;
Bodoky, I.; Jurícek, M. Org. Lett. 2017, 19, 3707.
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́
chez,
́
(
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K. S.; Lazzaroni, R.; Dehaen, W.; De Feyter, S. Nanoscale 2017, 9,
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8075.
ASSOCIATED CONTENT
■
(13) (a) Kaseyama, T.; Furumi, S.; Zhang, X.; Tanaka, K.; Takeuchi,
*
S
Supporting Information
M. Angew. Chem., Int. Ed. 2011, 50, 3684. (b) Hirose, T.; Ito, N.;
Kubo, H.; Sato, T.; Matsuda, K. J. Mater. Chem. C 2016, 4, 2811.
(
1
(
14) Buendía, J.; Calbo, J.; Ortí, E.; San
603880.
15) Valera, J. S.; Gom
(16) (a) García, F.; San
b) García, F.; Viruela, P. M.; Matesanz, E.; Ortí, E.; San
Eur. J. 2011, 17, 7755.
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18) Ten Eikelder, H. M. M.; Markvoort, A. J.; de Greef, T. F. A.;
́
chez, L. Small 2017, 13,
́
ez, R.; San
chez, L. J. Am. Chem. Soc. 2012, 134, 734.
chez, L. Chem.
́
chez, L. Small 2018, 14, 1702437.
Supplementary figures, experimental procedures, deriva-
́
⧧
(
-
́
tion of ΔG (T), and complete characterization (PDF)
(
AUTHOR INFORMATION
́
■
́
(
Hilbers, P. A. J. J. Phys. Chem. B 2012, 116, 5291.
(19) Korevaar, P. A.; Schaefer, C.; de Greef, T. F. A.; Meijer, E. W. J.
Am. Chem. Soc. 2012, 134, 13482.
ORCID
́
Notes
(
20) Buendía, J.; Greciano, E. E.; San
12444.
21) Xie, Z.; Stepanenko, V.; Radacki, K.; Wu
012, 18, 7060.
́
chez, L. J. Org. Chem. 2015, 80,
(
2
̈
rthner, F. Chem. - Eur. J.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
Financial support by the MINECO of Spain (CTQ2014-53046-
P and CTQ2017-82706-P) and the Comunidad de Madrid
■
(
NanoBIOSOMA, S2013/MIT-2807) is acknowledged. J.S.V.
thanks the MINECO for a predoctoral FPI grant.
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