Journal of the American Chemical Society
Page 10 of 12
(20) Yagai, S.; Iwai, K.; Karatsu, T.; Kitamura, A.
Angew. Chem. Int. Ed. 2012, 51, 9679–9683.
(21) Zhang, J.; Jin, J.; Zou, L.; Tian, H. Chem. Commun. 2013,
(51)
Chen, K.-Y.; Wezenberg, S. J.; Carroll, G. T.; London,
1
2
3
4
5
6
7
8
G.; Kistemaker, J. C. M.; Pijper, T. C.; Feringa, B. L. J. Org. Chem.
2014, 79, 7032–7040.
(52) Chen, J.; Chen, K.-Y.; Carroll, G. T.; Feringa, B. L.
Chem. Commun. 2014, 50, 12641–12644.
(53) Feringa, B. L. Acc. Chem. Res. 2001, 34, 504–513.
(54) Koumura, N.; Zijlstra, R. W. J.; van Delden, R. A.;
Harada, N.; Feringa, B. L. Nature 1999, 401, 152–155.
(55) Geertsema, E. M.; van der Molen, S. J.; Martens, M.;
Feringa, B. L. Proc. Natl. Acad. Sci. U. S. A. 2009, 106,
16919–16924.
49, 9926–9928.
(22) van Herpt, J. T.; Areephong, J.; Stuart, M. C. A.;
Browne, W. R.; Feringa, B. L. Chem. – Eur. J. 2014, 20, 1737–1742.
(23) Hirose, T.; Irie, M.; Matsuda, K. Adv. Mater. 2008, 20,
2137–2141.
(24) Klajn, R. Chem. Soc. Rev. 2014, 43, 148–184.
(25) Sousa, F. B. D.; Guerreiro, J. D. T.; Ma, M.; Anderson,
D. G.; Drum, C. L.; Sinisterra, R. D.; Langer, R. J. Mater. Chem.
2010, 20, 9910–9917.
9
(56) Valdes-Aguilera, O.; Neckers, D. C. Acc. Chem. Res.
1989, 22, 171–177.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(26) Florea, L.; Scarmagnani, S.; Benito-Lopez, F.; Diamond,
D. Chem. Commun. 2013, 50, 924–926.
(27) Liu, Y.; Fan, M.; Zhang, S.; Yao, J. J. Phys. Org. Chem.
2007, 20, 884–887.
(28) Zhang, Q.; Qu, D.-H.; Ma, X.; Tian, H. Chem. Commun.
2013, 49, 9800–9802.
(29) Ma, X.; Tian, H. Acc. Chem. Res. 2014, 47, 1971–1981.
(30) Zhang, Q.; Qu, D.-H.; Wu, J.; Ma, X.; Wang, Q.; Tian,
H. Langmuir 2013, 29, 5345–5350.
(57) Fink, R. F.; Seibt, J.; Engel, V.; Renz, M.; Kaupp, M.;
Lochbrunner, S.; Zhao, H.-M.; Pfister, J.; Würthner, F.; Engels, B.
J. Am. Chem. Soc. 2008, 130, 12858–12859.
(58) Kaiser, T. E.; Wang, H.; Stepanenko, V.; Würthner, F.
Angew. Chem. Int. Ed. 2007, 46, 5541–5544.
(59) Feringa, B. L. J. Org. Chem. 2007, 72, 6635–6652.
(60) Coleman, A. C.; Beierle, J. M.; Stuart, M. C. A.;
Maciá, B.; Caroli, G.; Mika, J. T.; van Dijken, D. J.; Chen, J.;
Browne, W. R.; Feringa, B. L. Nat. Nanotechnol. 2011, 6, 547–552.
Note that in this system, irradiation of the bis-thioxanthylidine
amphiphile led to irreversible cyclization and morphological
changes.
(31)
Xing, P.; Chen, H.; Bai, L.; Zhao, Y. Chem. Commun.
2015, 51, 9309–9312.
(32) Göstl, R.; Hecht, S. Chem. – Eur. J. 2015, 21, 4422–4427.
(33) Özçoban, C.; Halbritter, T.; Steinwand, S.; Herzig, L.-
M.; Kohl-Landgraf, J.; Askari, N.; Groher, F.; Fürtig, B.; Richter,
C.; Schwalbe, H.; Suess, B.; Wachtveitl, J.; Heckel, A. Org. Lett.
2015, 17, 1517–1520.
(34) Zou, Y.; Yi, T.; Xiao, S.; Li, F.; Li, C.; Gao, X.; Wu, J.; Yu,
M.; Huang, C. J. Am. Chem. Soc. 2008, 130, 15750–15751.
(35) London, G.; Chen, K.-Y.; Carroll, G. T.; Feringa, B. L.
Chem. – Eur. J. 2013, 19, 10690–10697.
(36) Chen, K.-Y.; Ivashenko, O.; Carroll, G. T.; Robertus, J.;
Kistemaker, J. C. M.; London, G.; Browne, W. R.; Rudolf, P.;
Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 3219–3224.
(37) Jiang, W.; Wang, G.; He, Y.; Wang, X.; An, Y.; Song, Y.;
Jiang, L. Chem. Commun. 2005, 28, 3550–3552.
(38) Eelkema, R.; Pollard, M. M.; Vicario, J.; Katsonis, N.;
Ramon, B. S.; Bastiaansen, C. W. M.; Broer, D. J.; Feringa, B. L.
Nature 2006, 440, 163.
(61)
Coleman, A. C.; Areephong, J.; Vicario, J.; Meetsma, A.;
Browne, W. R.; Feringa, B. L. Angew. Chem. Int. Ed. 2010, 49,
6580–6584.
(62) Israelachvili, J. N.; Mitchell, D. J.; Ninham, B. W.
J. Chem. Soc. Faraday Trans. 2 Mol. Chem. Phys. 1976, 72,
1525–1568.
(63) Hill, J. P.; Jin, W. S.; Kosaka, A.; Fukushima, T.;
Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.;
Aida, T. Science 2004, 304, 1481–1483.
(64) Jin, W.; Fukushima, T.; Niki, M.; Kosaka, A.; Ishii, N.;
Aida, T. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 10801–10806.
(65) Barton, D.; Willis, B. J. Chem. Soc.-Perkin Trans. 1 1972,
305–310.
(66) Buter, J.; Wassenaar, S; Kellogg, R. M. J. Org. Chem.
1972, 37, 4045–4060.
(39) Kudernac, T.; Ruangsupapichat, N.; Parschau, M.;
Maciá, B.; Katsonis, N.; Harutyunyan, S. R.; Ernst, K.-H.;
Feringa, B. L. Nature 2011, 479, 208–211.
(40) Li, Q.; Fuks, G.; Moulin, E.; Maaloum, M.; Rawiso, M.;
Kulic, I.; Foy, J. T.; Giuseppone, N. Nat. Nanotechnol. 2015, 10,
161–165.
(67) Klok, M.; Janssen, L. P.; Browne, W. R.; Feringa, B. L.
Faraday Discuss. 2009, 143, 319–334.
(68) ter Wiel, M. K. J.; Vicario, J.; Davey, S. G.; Meetsma, A.;
Feringa, B. L. Org. Biomol. Chem. 2005, 3, 28–30.
(69) Full-size cryo-TEM images are provided in the
Supporting Information; Figures S30–S47.
(41)
Wang, J.; Feringa, B. L. Science 2011, 331, 1429–1432.
(70) Chen, D.; Santore, M. M. Biochim. Biophys. Acta -
Biomembr. 2014, 1838, 2788–2797.
(42) Wezenberg, S. J.; Vlatković, M.; Kistemaker, J. C. M.;
Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 16784–16787.
(43) Browne, W. R.; Feringa, B. L. Nat. Nanotechnol. 2006,
1, 25–35.
(44) Pollard, M. M.; Klok, M.; Pijper, D.; Feringa, B. L.
Adv. Funct. Mater. 2007, 17, 718–729.
(45) Kulago, A. A.; Mes, E. M.; Klok, M.; Meetsma, A.;
Brouwer, A. M.; Feringa, B. L. J. Org. Chem. 2010, 75, 666–679.
(46) Klok, M.; Boyle, N.; Pryce, M. T.; Meetsma, A.; Browne,
W. R.; Feringa, B. L. J. Am. Chem. Soc. 2008, 130, 10484–10485.
(47) Vicario, J.; Meetsma, A.; Feringa, B. L. Chem. Commun.
2005, 47, 5910–5912.
(48) Koumura, N.; Geertsema, E. M.; van Gelder, M. B.;
Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124,
5037–5051.
(71)
Extrusion of the mixture did not lead to different
morphologies. All other samples were not extruded.
(72) Apart from nanotubes, a multilamellar vesicle (MLV) can
be seen in the top of Figure 3c. This is a spherical vesicle; most
likely from DOPC that is phase separated out.
(73) Xu, H.; Wang, Y.; Ge, X.; Han, S.; Wang, S.; Zhou, P.;
Shan, H.; Zhao, X.; Lu, J. R. Chem. Mater. 2010, 22, 5165–5173.
(74) Rodler, F.; Schade, B.; Jäger, C. M.; Backes, S.; Hampel,
F.; Böttcher, C.; Clark, T.; Hirsch, A. J. Am. Chem. Soc. 2015, 137,
3308–3317.
(75) As the PSS of 2 is very high (95:5), we believe that
effects on the morphology due to the presence of small amounts
of the other isomer are negligible.
(76) Nagarajan, R. Langmuir 2002, 18, 31–38.
(49) Bauer, J.; Hou, L.; Kistemaker, J. C. M.; Feringa, B. L.
J. Org. Chem. 2014, 79, 4446–4455.
(50) van Delden, R. A.; ter Wiel, M. K. J.; Pollard, M. M.;
Vicario, J.; Koumura, N.; Feringa, B. L. Nature 2005, 437,
1337–1340.
(77) Viseu, M. I.; Tatikolov, A. S.; Correia, R. F.;
Costa, S. M. B. J. Photochem. Photobiol. Chem. 2014, 280, 54–62.
(78) Goldstein, J.; Newbury, D. E.; Joy, D. C.; Lyman, C. E.;
Echlin, P.; Lifshin, E.; Sawyer, L.; Michael, J. R. Scanning Electron
ACS Paragon Plus Environment