The Journal of Organic Chemistry
Article
1493, 1327,1288, 968, 833, 752, 694, 553 cm−1. MALDI-TOF m/z:
calcd for [M + H]+, 452.205; found, 452.925.
3H), 6.97 (d, J = 8.0 Hz, 2H), 7.03−7.09 (m, 8H), 7.17 (d, J = 8.0 Hz,
1H), 7.26 (d, J = 8.0 Hz, 3H), 7.33 (t, J = 6.0 Hz, 4H), 7.52 (d, J = 8.0
Hz, 2H), 7.61 (d, J = 4.0 Hz, 2H), 7.90 (d, J = 8.0 Hz, 2H), 8.59 (s,
1H). 13C NMR (100 MHz, DMSO-d6, TMS): δ 162.2, 159.2, 147.9,
145.5, 139.3, 136.8, 132.1, 130.7, 129.7, 129.6, 127.8, 127.4, 124.7,
124.5, 123.6, 122.7, 121.7, 121.1, 114.5, 55.7. IR ν: 3426, 2922, 1589,
1509, 1492, 1277, 1170, 963, 837, 753, 695, 551 cm−1. HRMS (ESI-
MS) m/z: calcd for [M]+, 480.220; found, 480.227.
Preparation of Nanoaggregates. Stock THF solutions of the
compounds with a concentration of 10−3 mol L−1 were prepared.
Aliquots of the stock solution were transferred to 10 mL volumetric
flasks. After appropriate amounts of THF were added, water was added
dropwise under vigorous stirring to furnish 5 × 10−6 mol L−1 solutions
with different water contents (0−90 vol %). The UV−vis and PL
measurements of the resultant solutions were then performed
immediately.
Preparation of 3. Compound 3 was prepared according to a
procedure similar to that for 1, using 3-pyridinecarboxaldehyde (1 g,
9.35 mmol) instead of benzaldehyde, to produce 3.1 g of yellow needle
1
crystals. Yield: 90.0%. Mp: 181 °C. H NMR (DMSO-d6, 400 Hz): δ
6.97 (d, J = 8.0 Hz, 2H), 7.04−7.09 (m, 6H), 7.16 (t, J = 16.0 Hz, 1H),
7.24 (d, J = 16.0 Hz, 1H), 7.31−7.36 (m, 6H), 7.52−7.58 (m, 3H),
7.65 (d, J = 8.0 Hz, 2H), 8.33 (d, J = 8.0 Hz, 1H), 8.71 (d, J = 4.0 Hz,
1H), 8.78 (s, 1H), 9.07 (s, 1H). 13C NMR (100 MHz, DMSO-d6,
TMS): δ 157.8, 151.9, 150.4, 149.7, 146.9, 146.7, 135.8, 134.9, 131.6,
131.3, 129.6, 127.8, 127.6, 127.1, 126.2, 124.1, 123.3, 122.9, 121.7,
121.0. IR ν: 3029, 1591, 1509, 1488, 1330,1289, 965, 841, 759, 704,
552 cm−1. MALDI-TOF m/z: calcd for [M + H]+, 452.205; found,
452.990.
Preparation of 4. Compound 4 was prepared according to a
procedure similar to that for 1, using 4-pyridinecarboxaldehyde (1 g,
9.35 mmol) instead of benzaldehyde, to produce 2.5 g of orange
ASSOCIATED CONTENT
* Supporting Information
■
1
needle crystals. Yield: 72.5%. Mp: 180 °C. H NMR (DMSO-d6, 400
S
Hz): δ 6.97 (d, J = 8.0 Hz, 2H), 7.03−7.09 (m, 6H), 7.16 (d, J = 16.0
Hz, 1H), 7.25 (d, J = 16.0 Hz, 1H), 7.33 (t, J = 8.0 Hz, 4H), 7.38 (d, J
= 8.0 Hz, 2H), 7.53 (d, J = 8.0 Hz, 2H), 7.66 (d, J = 8.0 Hz, 2H), 7.86
(d, J = 8.0 Hz, 2H), 8.76 (s, 3H). 13C NMR (100 MHz, DMSO-d6,
TMS): δ 158.4, 150.5, 149.1, 146.9, 146.8, 142.5, 136.4, 131.2, 129.6,
128.1, 127.6, 127.2, 126.1, 124.2, 123.3, 122. 9, 122.1, 121.9. IR ν:
3029, 1591, 1515, 1495, 1330,1288, 966, 843, 765, 697, 559 cm−1.
MALDI-TOF m/z: calcd for [M + H]+, 452.205; found, 451.957.
Preparation of 5. Compound 5 was prepared according to a
procedure similar to that for 1, using salicylaldehyde (1.2 g, 9.83
mmol) instead of benzaldehyde, to give 2.0 g of orange-yellow powder.
Yield: 58.8%. Mp: 166 °C. 1H NMR (DMSO-d6, 400 Hz): δ 6.97 (d, J
= 8.0 Hz, 4H), 7.04−7.10 (m, 6H), 7.17 (d, J = 16.0 Hz, 1H), 7.26 (d,
J = 16.0 Hz, 1H), 7.33 (t, J = 8.0 Hz, 4H), 7.40−7.46 (m, 3H), 7.53 (d,
J = 8.0 Hz, 2H), 7.67 (d, J = 8.0 Hz, 3H), 9.03 (s, 1H), 13.18 (s, 1H).
13C NMR (100 MHz, DMSO-d6, TMS): δ 147.9, 147.6, 137.0, 133.5,
132.8, 131.6, 129.9, 129.7, 128.7, 127.8, 127.6, 126.3, 125.0, 124.1,
123.7, 123.6, 122.8, 122.0, 121.4, 119.5, 117.4. IR ν: 3027, 2922, 1617,
1590, 1508, 1490, 1329,1279, 1173, 964, 836, 754, 697, 538 cm−1.
HRMS (ESI-MS) m/z: calcd for [M]+, 466.205; found, 466.670.
Preparation of 6. Compound 6 was prepared according to a
procedure similar to that for 1, using 4-diethylaminobenzaldehyde (1.7
g, 9.60 mmol) instead of benzaldehyde, to produce 2.7 g of yellow
Spectroscopic data, absorption spectra, and fluorescence spectra
of 1−8 in five organic solvents; absorption and PL spectra of 2,
3, 4, 7, and 8 in THF/water mixtures with different water
fraction (fw); time-resolved fluorescence curves of 1−8;
changes in the integrals under the emission bands with
different water fractions; and NMR and mass spectra for
compounds 1−8. This material is available free of charge via the
AUTHOR INFORMATION
Corresponding Author
■
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by the Program for New Century
Excellent Talents in University (China), the Doctoral Program
Foundation of the Ministry of Education of China
(20113401110004), the National Natural Science Foundation
of China (21004001, 21271003, and 21271004), the Natural
Science Foundation of the Education Committee of Anhui
Province (KJ2012A024), the Natural Science Foundation of
Anhui Province (1208085MB22), the 211 Project of Anhui
University, the Ministry of Education Funded Projects Focus
on Returned Overseas Scholar, and Dr Startup funds of Anhui
University (33190077).
1
powder. Yield: 71.1%. Mp: 149 °C. H NMR (DMSO-d6, 400 Hz): δ
1.13 (s, 6H), 3.42 (m, 4H), 6.75 (d, J = 8.0 Hz, 2H), 6.97 (d, J = 8.0
Hz, 2H), 7.04−7.09 (m, 6H), 7.14−7.15 (m, 2H), 7.20 (d, J = 8.0 Hz,
2H), 7.31−7.35 (m, 4H), 7.52 (d, J = 12.0 Hz, 2H), 7.58 (d, J = 12.0
Hz, 2H), 7.72 (d, J = 8.0 Hz, 2H), 8.43 (s, 1H). 13C NMR (100 MHz,
DMSO-d6, TMS): δ 160.5, 159.6, 150.1, 148.0, 147.6, 132.2, 131.1,
130.3, 129.7, 127.6, 127.4, 127.3, 127.0, 124.9, 123.9, 123.4, 121.7,
111.5, 111.4, 44.9, 12.7. IR ν: 3024, 2972, 2929, 1586, 1524, 1509,
1491, 1431, 1356, 1272, 1177, 1152, 1076, 964, 827, 753, 697, 547
cm−1. HRMS (ESI-MS) m/z: calcd for [M]+, 522.283; found, 522.214.
Preparation of 7. Compound 7 was prepared according to a
procedure similar to that for 1, using 4-(diethylamino)salicylaldehyde
(1.9 g, 9.84 mmol) instead of benzaldehyde, to produce 2.5 g of brown
REFERENCES
■
(1) Shirota, Y. Z. J. Mater. Chem. 2005, 15, 75.
(2) Tao, S.; Li, L.; Yu, J. S.; Jiang, Y. D.; Zhou, Y. C.; Li, C. S.; Lee, S.
T.; Zhang, X. H.; Kwon, O. Chem. Mater. 2009, 21, 1284.
(3) Huang, J. H.; Su, J. H.; Li, X.; Lan, M. K.; Fung, K. M.; Fan, H.
H.; Cheah, K. W.; Chen, C. H.; Tian, H. J. Mater. Chem. 2011, 21,
2957.
1
powder. Yield: 63.8%. Mp: 169 °C. H NMR (DMSO-d6, 400 Hz): δ
1.12 (t, J = 6.0 Hz, 6H), 3.39 (m, 4H), 6.07 (s, J = 8.0 Hz, 1H), 6.33
(d, J = 8.0 Hz, 1H), 6.93−7.00 (m, 4H), 7.03−7.09 (m, 4H), 7.15−
7.22 (m, 2H), 7.24−7.28 (m, 2H), 7.31−7.34 (m, 6H), 7.52 (d, J = 8.0
Hz, 2H), 7.61 (d, J = 12.0 Hz, 2H), 8.74 (s, 1H), 12.67 (s, 1H). 13C
NMR (100 MHz, DMSO-d6, TMS): δ 160.5, 147.9, 147.7, 135.5,
134.2, 132.3, 132.0, 129.7, 127.8, 127.6, 126.7, 124.9, 124.2, 124.0,
123.8, 123.5, 121.5, 104.3, 97.8, 45.0. 12.9. IR ν: 3023, 2973, 2930,
1584, 1519, 1490, 1425, 1354, 1280, 1128, 965, 829, 754, 697, 545
cm−1. HRMS (ESI-MS) m/z: calcd for [M + H]+, 538.278; found,
538.008.
(4) Kim, E.; Park, S. B. Chem.Asian. J. 2009, 4, 1646.
(5) Qiang, F.; Zhang, C. L.; Zhang, Y. M.; He, W. J.; Gao, X.; Hu, P.;
Guo, Z. J. J. Am. Chem. Soc. 2009, 131, 1460.
(6) Mallick, A.; Haldar, B.; Chattopadhyay, N. J. Phys. Chem. B 2005,
109, 14684.
(7) Singh, R. B.; Mahanta, S.; Guchhait, N. Spectrochim. Acta, Part A
2009, 72, 1103.
Preparation of 8. Compound 8 was prepared according to a
procedure similar to that for 1, using p-anisaldehyde (1.3 g, 9.56
mmol) instead of benzaldehyde, to produce 1.5 g of yellow powder.
́
(8) Gomez-Esteban, S.; de la Cruz, P.; Aljarilla, A.; Arellano, L. M.;
Langa, F. Org. Lett. 2011, 13, 5362.
(9) Osaka, I.; Takimiya, K.; McCullough, R. D. Adv. Mater. 2010, 22,
4993.
1
Yield: 42.7%. Mp: 183 °C. H NMR (DMSO-d6, 400 Hz): δ 3.84 (s,
O
dx.doi.org/10.1021/jo401719c | J. Org. Chem. XXXX, XXX, XXX−XXX