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Journal of Materials Chemistry C
Page 6 of 8
ARTICLE
Journal Name
§ Z-scan measurements showed negligible intensity-dependent
0.019 mmol, 5 mol%) in toluene (5 mL) were added first a
solution of triphenylamine boronic acid (0.24 g, 0.84 mmol, 2.3
eq) in methanol (1.5 mL) and then a aqueous solution of sodium
carbonate (2 M, 0.8 mL). The reaction mixture was stirred at 80
°C under argon for 48 hours. A solution of saturated ammonium
chloride (100 mL) was added and organic compounds were
response of these three chromophores at 83D0OnIm: 10is.10o3ri9g/iCn5aTtCed00f5ro31mK
two-photon absorption process and the contribution of excited
state absorption or other higher nonlinear process is minimal.
1
2
R. A. Carboni and R. V. Lindsey, J. Am. Chem. Soc., 1959, 81,
4342.
extracted with dichloromethane (2100 mL). The combined
G. L. Rusinov, R. I. Ishmetova, N. I. Latosh, I. N. Ganebnych, O.
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355.
organic phases were washed with a saturated solution of
sodium chloride (250 mL), dried over anhydrous sodium sulfate,
filtrated and concentrated under reduced pressure. The crude
product was purified by a silicagel column chromatography
,
3
4
5
6
N. Saracoglu, Tetrahedron, 2007, 63, 4199.
D. L. Boger, Tetrahedron, 1983, 39, 2869.
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(CH2Cl2/PE: 6.5/3.5) to give two orange solids
g)) and (Yield: 42% (0.13 g)). Characterizations of
IR (
max/cm-1): 2923, 2853, 1591, 1548, 1492, 1461, 1329, 1282,
5
(Yield: 57% (0.20
,
6
5
: mp: 90 °C;
7
8
T. J. Sparey and T. Harrison, Tetrahedron Lett., 1998, 39, 5873.
E. Gomez-Bengoa, M. D. Helm, A. Plant and J. P. A. Harrity, J.
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1180, 1070, 837; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.12 (s, 2H),
7.38 (d, J=8.7 Hz, 4H), 7.31 (dd, J=8.2 and 7.8 Hz, 8H), 7.18 (d,
J=7.8 Hz, 8H), 7.12 (d, J=8.7 Hz, 4H), 7.08 (t, J=7.3Hz, 4H), 2.75
(t, J=7.8 Hz, 4H), 1.65 (tt, J=7.3 and 6.9 Hz, 4H), 1.40-1.27 (m,
28H), 0.89 (t, J=6.8 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ (ppm):
161.1, 148.1, 147.4, 145.9, 140.5, 133.3, 132.8, 129.9, 129.5,
127.2, 125.1, 123.6, 122.6, 32.0, 30.1, 29.7 (2C), 29.6 (2C), 29.5,
29.0, 22.8, 14.3; HRMS-MALDI (m/z): (M)•+ calcd for C66H72N6S2,
9
U. Rohr, J. Schatz and J. Sauer, Eur. J. Org. Chem., 1998, 1998,
2875.
10 L. A. Paquette, W. R. S. Barton and J. C. Gallucci, Org. Lett.,
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12 R. Troschütz and J. Müller, Synthesis, 2006, 2006, 1513.
13 L. I. Robins, R. D. Carpenter, J. C. Fettinger, M. J. Haddadin, D.
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16 A. Mangia, F. Bortesi and U. Amendola, J. Heterocycl. Chem.,
1977, 14, 587.
1012.5254, found 1012.5240; UV-vis (CH2Cl2) λmax
(49100 L.mol-1.cm-1) and 441 nm (49300 L.mol-1.cm-1);
Characterizations of : mp: <50 °C; IR (
max/cm-1): 2962, 2924,
(ε) = 306 nm
6
2853, 1592, 1550, 1492, 1465, 1330, 1261, 1095, 1071, 1018,
800; 1H NMR (400 MHz, CDCl3) δ (ppm): 8.12 (s, 1H), 8.08 (s, 1H),
7.37 (d, J=8.7 Hz, 2H), 7.30 (dd, J=8.2 and 7.3 Hz, 4H), 7.17 (dd,
J=8.7 and 0.9 Hz, 4H), 7.12 (d, J=8.7 Hz, 2H), 7.08 (t, J=7.3 Hz,
2H), 2.74 (t, J=7.3 Hz, 2H), 2.69 (t, J=7.3 Hz, 2H), 1.75-1.65 (m,
4H), 1.39-1.19 (m, 28H), 0.88 (t, J=6.8 Hz, 3H), 0.87 (t, J=6.8 Hz,
3H); 13C NMR (100 MHz, CDCl3) δ (ppm): 161.5, 161.2, 148.2,
147.4, 146.1, 145.6, 140.6, 135.8, 133.5, 132.6, 132.8, 130.0,
129.6, 127.5, 127.1, 125.2, 123.7, 122.6, 32.1(2C), 30.9(2C),
30.5(2C), 29.8(2C), 29.7(2C), 29.5(2C), 29.4(2C), 29.0(2C),
22.8(2C), 14.3(2C); HRMS-MALDI (m/z): (M)•+ calcd for
C48H58BrN5S2, 847.3317, found 847.3298 (100%); UV-vis (CH2Cl2)
17 S. C. Benson, L. Lee, L. Yang and J. K. Snyder, Tetrahedron,
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18 C. Quinton, V. Alain-Rizzo, C. Dumas-Verdes, F. Miomandre
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22 M. Glöckle and W. Kaim, Angew. Chem. Int. Ed., 1999, 38
,
3072.
λmax(ε
) = 305 nm (34800 L.mol-1.cm-1), 354 nm (34000 L.mol-
1.cm-1) and 441 nm (25100 L.mol-1.cm-1)
23 M. Glöckle, W. Kaim and J. Fiedler, Z. Anorg. Allg. Chem., 2001,
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24 O. Schneider and M. Hanack, Angew. Chem., 1983, 95, 804.
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26 F. Miomandre, E. Lépicier, S. Munteanu, O. Galangau, J. F.
Audibert, R. Méallet-Renault, P. Audebert and R. B. Pansu,
Acknowledgements
C. Q, V. A.-R, C. D.-V, G. C and P. A thank the CNRS and the
ACS Appl. Mater. Interfaces, 2011, 3, 690.
Ministry of French Research for funding the project. S.-H. C and 27 F. Miomandre, C. Allain, G. Clavier, J.-F. Audibert, R. B. Pansu,
P. Audebert and F. Hartl, Electrochem. Commun., 2011, 13
574.
,
J.W. P thanks the support of DARPA ZOE program (Grant No.
W31P4Q-09-1-0012). Mr. J. Fromont and Dr. O. Galangau are
thanked for technical assistance with calculations.
28 C. Dumas-Verdes, F. Miomandre, E. Lépicier, O. Galangau, T.
T. Vu, G. Clavier, R. Méallet-Renault and P. Audebert, Eur. J.
Org. Chem., 2010, 2010, 2525.
29 F. Miomandre, R. Meallet-Renault, J. J. Vachon, R. B. Pansu
and P. Audebert, Chem. Commun., 2008, 16, 1913.
30 Y. Kim, E. Kim, G. Clavier and P. Audebert, Chem. Commun.,
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31 Y. Kim, J. Do, E. Kim, G. Clavier, L. Galmiche and P. Audebert,
J. Electroanal. Chem., 2009, 632, 201.
32 S. Seo, Y. Kim, Q. Zhou, G. Clavier, P. Audebert and E. Kim, Adv.
Funct. Mater., 2012, 22, 3556.
33 J. Malinge, C. Allain, L. Galmiche, F. Miomandre and P.
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Notes and references
‡ The ND-2PA measured two-photon cross section (δND) should be
2× larger than the z-scan measured degenerate two-photon cross
section (δD). Detailed calculation is shown in reference 53 and 54
.
However, due to the group velocity mismatch between the visible
probe wavelengths and the near IR excitation wavelength,
quantative determination of two-photon absorption cross sections
using ND-2PA spectrometer is dubious.
6 | J. Name., 2012, 00, 1-3
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