You have already added 0 works in your ORCID record related to the merged Research product.
You have already added 0 works in your ORCID record related to the merged Research product.
Controllability of dynamic double helices: quantitative analysis of the inversion of a screw-sense preference upon complexation
Copyright policy )Controllability of dynamic double helices: quantitative analysis of the inversion of a screw-sense preference upon complexation
We describe a quantitative analysis of the complexation-induced inversion of a screw-sense preference based on a conformationally dynamic double-helix structure in a macrocycle. The macrocycle is composed of two twisting units (terephthalamide), which are spaced by two strands (1,3-bis(phenylethynyl)benzene), and is designed to generate a double-helix structure through twisting about a C 2 axis in a conrotatory manner. The attachment of chiral auxiliaries to the twisting units induces a helical preference for a particular sense of (M)- or (P)-helicity through the intramolecular transmission of chirality to dynamic double helices. The twisting unit can also act as a binding site for capturing a guest molecule, and, in a complexed state, the preferred screw sense of the dynamic double-helix structure is reversed to exhibit the contrary preference. We quantitatively monitored the complexation-induced inversion of the screw-sense preference using 1H NMR spectroscopy, which enabled us to observe independently two species with (M)- or (P)-helicity in both the absence and presence of a guest molecule. Inversion of the screw-sense preference was induced upon complexation with an achiral guest as well as a chiral guest.
We analyzed quantitatively the complexation-induced inversion of a screw-sense preference of dynamic double helices with CD and 1H NMR spectroscopy.
Microsoft Academic Graph classification: Stereochemistry Chemistry Sense (electronics) Inversion (discrete mathematics) Preference Controllability Crystallography Intramolecular force Molecule Conrotatory and disrotatory Chirality (chemistry)
General Chemistry, Chemistry
General Chemistry, Chemistry
Microsoft Academic Graph classification: Stereochemistry Chemistry Sense (electronics) Inversion (discrete mathematics) Preference Controllability Crystallography Intramolecular force Molecule Conrotatory and disrotatory Chirality (chemistry)
2813
Albrecht, M., Haldar, D., Schmuck, C., Furusho, Y., Yashima, E., Su, D. S.. Angew. Chem., Int. Ed.. 2011; 50: 4747 [OpenAIRE] [PubMed]
Goto, H., Katagiri, H., Furusho, Y., Yashima, E., Haldar, D., Jiang, H., Léger, J.-M., Huc, I., Gan, Q., Ferrand, Y., Chandramouli, N., Kauffmann, B., Aube, C., Dubreuil, D., Huc, I., Yamada, H., Wu, Z.-Q., Furusho, Y., Yashima, E., Prabhakaran, P., Priya, G., Sanjayan, G. J., Shinozaki, Y., Richards, G., Ogawa, K., Yamano, A., Ohara, K., Yamaguchi, K., Kawano, S., Tanaka, K., Araki, Y., Wada, T., Otsuki, J., Singleton, M. L., Pirotte, G., Kauffmann, B., Ferrand, Y., Huc, I., Miyagawa, M., Ichinose, W., Yamaguchi, M.. Chem.–Eur. J.. 2014; 20: 1272 [OpenAIRE] [PubMed]
Malinovskii, V. L., Samain, F., Häner, R., Sugimoto, T., Suzuki, T., Shinkai, S., Sada, K., Maeda, T., Furusho, Y., Sakurai, S.-I., Kumaki, J., Okoshi, K., Yashima, E.. J. Am. Chem. Soc.. 2008; 130: 7938
Rajca, A., Andrej, A., Rajca, S., Shoemaker, R., Marsella, M. J., Kim, I. T., Tham, F.. J. Am. Chem. Soc.. 2000; 122: 974
Fenton, D. E., Matthews, R. W., McPartlin, M., Murphy, B. P., Scowen, I. J., Tasker, P. A., Matthews, R. W., McPartlin, M., Scowen, I. J.. Chem. Commun.. 1996: 309
Fox, J. M., Lin, D., Itagaki, Y., Fujita, T., Mascal, M., Moody, C. J., Morrell, A. I., Slawin, A. M. Z., Williams, D. J., Mascal, M., Wood, I. G., Begley, M. J., Batsanov, A. S., Walsgrove, T., Slawin, A. M. Z., Williams, D. J., Drake, A. F., Siligardi, G., An, D. L., Nakano, T., Orita, A., Otera, J., Lin, F., Peng, H.-Y., Chen, J.-X., Chik, D. T. W., Cai, Z., Wong, K. M. C., Yam, V. W. W., Wong, H. N. C., Maeda, H., Nishimura, T., Akuta, R., Takaishi, K., Uchiyama, M., Muranaka, A.. Chem. Sci.. 2013; 4: 1204
Katoono, R., Kawai, H., Fujiwara, K., Suzuki, T., Katoono, R., Kusaka, K., Fujiwara, K., Suzuki, T., Katoono, R., Kusaka, K., Kawai, S., Tanaka, Y., Hanada, K., Nehira, T., Fujiwara, K., Suzuki, T., Katoono, R., Kawai, H., Fujiwara, K., Suzuki, T., Katoono, R., Fujiwara, K., Suzuki, T., Katoono, R., Tanaka, Y., Kusaka, K., Fujiwara, K., Suzuki, T.. J. Org. Chem.. 2015; 80: 7613-7625 [OpenAIRE] [PubMed]
Yashima, E., Matsushima, T., Okamoto, Y., Inai, Y., Ousaka, N., Okabe, T., Inai, Y., Komori, H.. Biomacromolecules. 2004; 5: 1231 [OpenAIRE] [PubMed]
citations This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).17 popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.Average influence This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).Average impulse This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.Top 10% citations This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).17 popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.Average influence This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).Average impulse This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.Top 10%
Citations provided by BIP!Popularity provided by BIP!We describe a quantitative analysis of the complexation-induced inversion of a screw-sense preference based on a conformationally dynamic double-helix structure in a macrocycle. The macrocycle is composed of two twisting units (terephthalamide), which are spaced by two strands (1,3-bis(phenylethynyl)benzene), and is designed to generate a double-helix structure through twisting about a C 2 axis in a conrotatory manner. The attachment of chiral auxiliaries to the twisting units induces a helical preference for a particular sense of (M)- or (P)-helicity through the intramolecular transmission of chirality to dynamic double helices. The twisting unit can also act as a binding site for capturing a guest molecule, and, in a complexed state, the preferred screw sense of the dynamic double-helix structure is reversed to exhibit the contrary preference. We quantitatively monitored the complexation-induced inversion of the screw-sense preference using 1H NMR spectroscopy, which enabled us to observe independently two species with (M)- or (P)-helicity in both the absence and presence of a guest molecule. Inversion of the screw-sense preference was induced upon complexation with an achiral guest as well as a chiral guest.
We analyzed quantitatively the complexation-induced inversion of a screw-sense preference of dynamic double helices with CD and 1H NMR spectroscopy.