New Journal of Chemistry
Page 4 of 6
Journal Name
ARTICLE
Chemistry Research Unit (EXPL/QEQ-SUP/1041/2013) and
the Portuguese National NMR Network (RNRMN). SG also
thanks
the
FCT
for
a
DOI: 10.1039/C6NJ01387B
(SFRH/BPD/70702/2010).
Notes and references
a
University of Aveiro, QOPNA, Department of Chemistry, 3810-193
Aveiro, Portugal. E-mail: artur.silva@ua.pt; sguieu@ua.pt
b
University of Aveiro, CICECO, Department of Chemistry, 3810-193
†
Electronic Supplementary Information (ESI) available: [Synthetic
procedures, NMR spectra, absorption and emission spectra, AIEE tests
and crystal structures]. See DOI: 10.1039/b000000x/
1 X. Zhan, N. Sun, Z. Wu, J. Tu, L. Yuan, X. Tang, Y. Xie, Q. Peng, Y.
Dong, Q. Li, D. Ma, Z. Li, Chem. Mater., 2015, 27, 1847.
2 M. Grätzel, Prog. Photovolt. Res. Appl., 2000, 8, 171.
Figure 5 Crystal structure of 2b and 2d. Asymmetric unit of 2b
(a) and 2d (b), crystal packing of 2b (c) and 2d (d). Thermal
ellipsoids are shown at the 50% probability level, hydrogen
atoms are shown with an arbitrary radius (0.30Å). C, grey; O,
red; N, blue; H, white; Br, brown; Cl, green. Short contacts
shown as black lines.
3
N. Zhao, M. Li, Y. Yan, J. W. Y. Lam, Y. L. Zhang, Y. S. Zhao, K. S.
Wong, B. Z. Tang, J. Mater. Chem. C, 2013, 1, 4640.
4 I. Capek, Adv. Colloid Interface Sci., 2002, 97, 91.
5
F. Mancin, P. Scrimin, P. Tecilla, U. Tonellato, Coord. Chem. Rev.,
In conclusion, a family of halogenated chalcones has been
synthesized and their structures fully characterized, including,
for two of them, the crystal structure. The optoelectronic
properties of these materials have been studied in solution, in
aggregate form and in the solid state. The compounds bearing a
dimethylamino substituent present a strong push-pull character
and fair quantum yields in solution and in the solid state. All
compounds exhibit AIEE, their photoluminescence intensity
increasing upon aggregation in mixed solvent up to a hundred
fold. This property has been rationalized on the basis of the
crystal structures obtained for two chromophores. The presence
of halogen atoms, usually quenching the emission through the
heavy atom effect, has little effect on the emission properties of
these chromophores in solution. In the solid state, the presence
of halogen atoms enhances the emission, probably by changing
the packing of the dyes.
2009, 253, 2150.
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S. W. Thomas III, G. D. Joly, T. M. Swager, Chem. Rev., 2007, 107,
1339.
7
P.-I. Shih, C.-L. Chiang, A. K. Dixit, C.-K. Chen, M.-C. Yuan, R.-Y
Lee, C.-T. Chen, E. W.-G. Diau, C.-F. Shu, Org. Lett., 2006, 8, 2799.
8 C.-T. Chen, Chem. Mater., 2004, 16, 4389.
9 B.-K. An, J. Gierschner, S.Y. Park, Acc. Chem. Res., 2012, 45, 544.
10
W. Z.. Yuan, X. Y. Shen, H. Zhao, J. W. Y. Lam, L. Tang, P. L. C.
Wang, Y. Liu, Z. Wang, Q. Zheng, J. Z. Sun, Y. Ma, B. Z. Tang, J.
Phys. Chem. C, 2010, 114, 6090; J. Luo, Z. Xie, J. W. Y. Lam, L.
Cheng, H. Chen, C. Qiu, H. Sing Kwok, X. Zhan, Y. Liu, D. Zhu, B.
Z. Tang, Chem. Commun., 2001, 1740; Y. Hong, J. W. Y. Lam, B. Z.
Tang, Chem. Soc. Rev., 2011, 40, 5361; J. Yang, J. Huang, Q. Li, Z.
Li, J. Mater. Chem. C, 2016, 4, 2663; J. Mei, N. L. C. Leung, R. T.
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Acknowledgements
11
S. Guieu, J. Rocha , A. M. S. Silva , Tetrahedron Lett., 2013, 54, 2870;
This work was developed within the scope of the projects
CICECO-Aveiro Institute of Materials (Ref. FCT UID/CTM
S. Guieu, J. Rocha, A. M. S. Silva, Tetrahedron, 2013, 69, 9329.
12
O. Bolton, K. Lee, H.-J. Kim, K. Y. Lin, J. Kim, Nature Chem., 2011,
/50011/2013)
and
UI
QOPNA
(Ref.
FCT
3, 205.
UID/QUI/00062/2013), financed by national funds through the
FCT/MEC and when appropriate co-financed by FEDER under
the PT2020 Partnership Agreement. Thanks are due to the
University of Aveiro and the Portuguese Fundação para a
Ciência e a Tecnologia (FCT) for funding the Organic
13
R. Nithya, N. Santhanamoorthi, P. Kolandaivel, K. Senthilkumar, J.
Phys. Chem. A, 2011, 115, 6594.
4 | New J. Chem., 2015, 00, 1-5
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