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Journal Name
Dalton Transactions
DOI: 10.1039/C5DT00434A
Confocal images were acquired at the Spectrography and
Bioimaging Facility, NIBB Core Research Facilities. The
Computations were performed using Research Center for
Computational Science, Okazaki, Japan. This work was
supported by the JST-CREST and JST-ACCEL programs.
Beaupérin, S. Saleh, A. Job, J. Andrieu and M. Picquet, C. R. Chimie
2013, 16, 580.
,
7
8
M. Kuritani, S. Tashiro and M. Shionoya, Chem. Asian. J. 2013, 8,
1368.
In general, the size and shape of self-assembled architectures depend
on the self-assembling conditions (temperature, pH, solvent,
concentration, etc), though the correlation between the conditions and
shape and/or size of the resulting assemblages is still unclear. For
selected examples, see (a) P. L. Soo and A. Eisenberg, J. Polym. Sci.
Part B: Polym. Phys. 2004, 42, 923; (b) G. Fernández, F. García and
L. Sánchez, Chem. Commun. 2008, 6567; (c) T. Wang, J. Jiang, Y.
Liu, Z. Li and M. Liu, Langmuir 2010, 26, 18694; (d) L. Jia, D. Lévy,
D. Durand, M. Impéror-Clerc, A. Cao and M.-H. Li, Soft Matter 2011,
Notes and references
a
Institute for Molecular Science, Okazaki 444-8787, Japan. FAX: +81
564 59 5574; E-mail: uo@ims.ac.jp
b SOKENDAI (The Graduate University for Advanced Studies), Okazaki
444-8787, Japan
c
Green Nanocatalysis Research Team, RIKEN Center for Sustainable
Resource Science, Wako 351-0198, Japan
7
, 7395; (e) L. Martín, E. Castro, A. Ribeiro, M. Alonso and J. C.
Rodríguez-Cabello, Biomacromolecules, 2012, 13, 293; (f) P. Koley
and A. Pramanik, Soft Matter 2012, , 5364; (g) T. Sakai, R. Ikoshi,
†
Electronic Supplementary Information (ESI) available: Experimental
8
details, additional TEM images and spectroscopic data for all products.
See DOI: 10.1039/b000000x/
N. Toshida and M. Kagaya, J. Phys. Chem. B 2013, 117, 5081. See
also ref. 2a.
9
The molecular structures of 2a and 2b were preliminarily calculated
1
2
(a) D. D. Lasic, Biochem. J. 1988, 256, 1; b) D. D. Lasic, Trends
Biotechnol. 1998, 16, 307; (c) A. Mueller and D. F. O’Brien, Chem.
by RHF/STO-3G
10 For pioneering studies on the arylation of terminal alkynes in water,
see: (a) Y. Uozumi and Y. Kobayashi, Heterocycles 2003, 59, 71; (b)
C. Nájera, J. Gil-Moltó, S. Karlström and L. R. Falvello, Org. Lett.
Rev. 2002, 102, 727; (d) C.-P. Chng, Soft Matter 2013, 9, 7294; (e) E.
Busseron, Y. Ruff, E. Moulin, N. Giuseppone, Nanoscale 2013, 5,
7098.
2003, 5, 1451.
(a) J. P. Hill, W. Jin, A. Kosaka, T. Fukushima, H. Ichihara, T.
Shimomura, K. Ito, T. Hashizume, N. Ishii and T. Aida, Science
2004, 304, 1481; (b) W. Jin, T. Fukushima, M. Niki, A. Kosaka, N.
Ishii and T. Aida, Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 10801;
(c) T. Yamamoto, T. Fukushima, Y. Yamamoto, A. Kosaka, W. Jin,
N. Ishii and T. Aida, J. Am. Chem. Soc. 2006, 128, 14337; (d) X.
Zhang, Z. Chen and F. Würthner, J. Am. Chem. Soc. 2007, 129, 4886;
(e) K. V. Rao and S. J. George, Org. Lett. 2010, 12, 2656.
11 Typical procedure for the arylation of terminal alkynes: To a vial
equipped with a screw cap, 1 mL aqueous suspension of 2avscl (1.0
mg, 8.5 × 10-4 mmol), triethylamine (10.3 mg, 0.10 mmol),
ethynylbenzene (11a) (7.0 mg, 0.068 mmol), and iodobenzene (10a
)
(6.9 mg, 0.034 mmol) were added. The reaction mixture was agitated
with shaking at 40 °C for 1 h and allowed to cool to 25 °C. The
reaction mixture was extracted with tert-butyl-methyl ether (1.0 mL,
5 times). The combined organic layer was dried over Na2SO4 and
concentrated under reduced pressure. The resulting residue was
chromatographed on silica gel (eluent: hexane) to give 1,1'-ethyne-
1,2-diyldibenzene 12a (11.5 mg, 0.063 mmol, 92%) as white solids.
12 We also tested the coupling reaction of 10a with 11a in the presence
3
4
For reviews on catalytic reactions with vesicles, see: (a) D. M.
Vriezema, M. C. Aragonès, J. A. A. W. Elemans, J. J. L. M.
Cornelissen, A. E. Rowan and R. J. M. Nolte, Chem. Rev. 2005, 105
,
1445; (b) M. Raynal, P. Ballester, A. Vidal-Ferran and P. W. N. M.
van Leeuwen, Chem. Soc. Rev. 2014, 43, 1734.
of 1avscl, 1aamps, 1bvscl, and 1bamps in water under the similar reaction
For selected recent examples of catalytic applications of vesicles, see:
(a) D. M. Vriezema, P. M. L. Garcia, N. S. Oltra, N. S. Hatzakis, S.
M. Kuiper, R. J. M. Nolte, A. E. Rowan and J. C. M. van Hest,
Angew. Chem. Int. Ed. 2007, 46, 7378; (b) G. Delaittre, I. C.
Reynhout, J. J. L. M. Cornelissen and R. J. M. Nolte, Chem. Eur. J.
2009, 15, 12600; (c) L. Qin, L. Zhang, Q. Jin, J. Zhang, B. Han and
M. Liu, Angew. Chem. Int. Ed. 2013, 52, 7761; (d) M. C. M. van
Oers, L. K. E. A. Abdelmohsen, F. P. J. Rutjes and J. C. M. van Hest,
Chem. Commun. 2014, 50, 4040.
conditions for Table 1 to give 12a in 34, 29, 23, and 27% yield,
respectively. The formation of vesicles from 1a and 1b did not
accelerate the reaction.
13 After the reaction, TEM analysis showed that the vesicular structure
of 2avscl was maintained (see Electric Supplementary Information).
14 For TEM images of 2aamps and 2bamps, see Electronic Supplementary
Information.
15 The reaction of bromobenzene with ethynylbenzene (11a) with 2avscl
(40 °C for 24 h in water) gave 1,1'-ethyne-1,2-diyldibenzene (12a) in
21% yield.
5
6
(a) G. Hamasaka, T. Muto and Y. Uozumi, Angew. Chem. Int. Ed.
2011, 50, 4876; (b) G. Hamasaka, T. Muto and Y. Uozumi, Dalton
Trans. 2011, 40, 8859; (c) G. Hamasaka and Y. Uozumi, Chem.
Commun. 2014, 50, 14516.
16 The reaction of iodobenzene (10a) with 1-n-heptyne with 2avscl
(40 °C for 24 h in water) gave 1-heptyn-1-yl-benzene in only 22%
yield.
For selected reviews on the arylation of terminal alkynes, see (a) K.
Sonogashira, J. Organomet. Chem. 2002, 653, 46; (b) H. Doucet and
J.–C. Hierso, Angew. Chem. Int. Ed. 2007, 46, 834; (c) R. Chinchilla
and C. Nájera, Chem. Rev. 2007, 107, 874; (d) R. Chinchilla and C.
Nájera, Chem. Soc. Rev. 2011, 40, 5084; (e) J.-C. Hierso, M.
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