Share This Article:

Synthesis and Photophysical Properties of 9,10-Disubstituted Anthracenes

Abstract Full-Text HTML Download Download as PDF (Size:1056KB) PP. 943-952
DOI: 10.4236/msa.2015.611095    2,871 Downloads   3,378 Views  

ABSTRACT

We report the synthesis and photophysical characterization of four 9,10-disubstituted dipheny-lanthracenes with specific modifications of the model backbone which involve both the 9,10 para substituents at the phenyl rings and the substitution with carbon-carbon triple bonds. The effects of such modifications on the photoluminescence and electroluminescence properties have been investigated on the basis of the diphenylanthracene molecular characteristics and in view of application to light-emitting devices. We have found that the substitution with the carbon-carbon triple bonds at the two 9,10-phenyls noticeably alters the electronic states of the reference molecule, also introducing a certain degree of sensitivity to the phenyl substituents, which improves the tunability of the optical emission. Differently, the 9,10 para substituents produce minor changes in the single-molecule properties, due to the lack of electronic conjugation across the 9,10-phenyls. However, even a single nitro substituent in the phenyl para position produces the formation of excimers, which appreciably reduces the optical quantum efficiency. These properties are maintained in solid-state blends and simple spin-coated bilayer electroluminescent devices have been fabricated.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Pizzoferrato, R. , Tagliatesta, P. , Schillaci, C. , Prosposito, P. and Angelis, R. (2015) Synthesis and Photophysical Properties of 9,10-Disubstituted Anthracenes. Materials Sciences and Applications, 6, 943-952. doi: 10.4236/msa.2015.611095.

References

[1] Agbandje, M., Jenkins, T.C., McKenna, R., Reszka, A.P. and Neidle, S. (1992) Anthracene-9,l O-Diones as Potential Anticancer Agents. Synthesis, DNA-Binding, and Biological Studies on a Series of 2,6-Disubstituted Derivatives. Journal of Medicinal Chemistry, 35, 1418-1429.
http://dx.doi.org/10.1021/jm00086a010
[2] Becker, H.D. (1993) Unimolecular Photochemistry of Anthracenes. Chemical Reviews, 93, 145-172.
http://dx.doi.org/10.1021/cr00017a008
[3] Valeur, B. (2002) Molecular Fluorescence: Principles and Applications. Wiley-VCH, Weinheim.
[4] Meng, H., Sun, F.P., Goldfinger, M.B., Jaycox, G.D., Li, Z.G., Marshall, W.J. and Blackman, G.S. (2005) High-Performance Stable Organic Thin-Film Field-Effect Transistors Based on Bis-5’-alkylthiophen-2’-yl-2,6-Anthracene Semiconductors. Journal of the American Chemical Society, 127, 2406-2407.
http://dx.doi.org/10.1021/ja043189d
[5] Teng, C., Yang, X., Yang, C., Li, S., Cheng, M., Hagfeldt, A. and Sun, L. (2010) Molecular Design of Anthracene-Bridged Metal-Free Organic Dyes for Efficient Dye-Sensitized Solar Cells. Journal of Physical Chemistry C, 114, 9101-9110.
http://dx.doi.org/10.1021/jp101238k
[6] Shi, J. and Tang, C.W. (2002) Anthracene Derivatives for Stable Blue-Emitting Organic Electroluminescence Devices. Applied Physics Letters, 80, 3201-3203.
http://dx.doi.org/10.1063/1.1475361
[7] Serevicius, T., Komskis, R., Adomenas, P., Adomeniene, O., Jankauskas, V., Gruodis, A., Kazlauskas, K. and Jursenas, S. (2014) Non-Symmetric 9,10-Diphenylanthracene-Based Deep-Blue Emitters with Enhanced Charge Transport Properties. Physical Chemistry Chemical Physics, 16, 7089-7101.
http://dx.doi.org/10.1039/c4cp00236a
[8] Lin, S.H., Wu, F.I. and Liu, R.S. (2009) Synthesis, Photophysical Properties and Color Tuning of Highly Fluorescent 9,10-Disubstituted-2,3,6,7-Tetraphenylanthracene. Chemical Communications, 6961-6963.
http://dx.doi.org/10.1039/b912289c
[9] Zhou, X., Piland, G.B., Kurunthu, D., Dillon, R.J., Burdett, J.J. and Bardeen, C.J. (2012) The Photophysics of the 2,6 Dialkoxy Anthracenes: Evidence for Excited State Side-Chain Conformational Relaxation. Journal of Luminescence, 132, 2997-3003.
http://dx.doi.org/10.1016/j.jlumin.2012.06.012
[10] Mallesham, G., Balaiah, S., Ananth Reddy, M., Sridhar, B., Singh, P., Srivastava, R., Bhanuprakash, K. and Jayathirtha Rao, V. (2014) Design and Synthesis of Novel Anthracene Derivatives as n-Type Emitters for Electroluminescent Devices: A Combined Experimental and DFT Study. Photochemical & Photobiological Sciences, 13, 342-357.
http://dx.doi.org/10.1039/c3pp50284h
[11] Kim, R., Lee, S., Kim, K.H., Lee, Y.J., Kwon, S.K., Kim, J.J. and Kim, Y.H. (2013) Extremely Deep Blue and Highly Efficient Non-Doped Organic Light Emitting Diodes Using an Asymmetric Anthracene Derivative with a Xylene Unit. Chemical Communications, 49, 4664.
http://dx.doi.org/10.1039/c3cc41441h
[12] Fukagawa, H., Shimizu, T., Ohbe, N., Tokito, S., Tokumaru, K. and Fujikake, H. (2012) Anthracene Derivatives as Efficient Emitting Hosts for Blue Organic Light-Emitting Diodes Utilizing Triplet-Triplet Annihilation. Organic Electronics, 13, 1197-1203.
http://dx.doi.org/10.1016/j.orgel.2012.03.019
[13] Chiang, C.J., Kimyonok, A., Etherington, M.K., Griffiths, G.C., Jankus, V., Turksoy, F. and Monkman, A.P. (2013) Ultrahigh Efficiency Fluorescent Single and Bi-Layer Organic Light Emitting Diodes: The Key Role of Triplet Fusion. Advanced Functional Materials, 23, 739-746.
http://dx.doi.org/10.1002/adfm.201201750
[14] Wu, C.L., Chang, C.H., Chang, Y.T., Chen, C.T., Chen, C.T. and Su, C.J. (2014) High Efficiency Non-Dopant Blue Organic Light-Emitting Diodes Based on Anthracene-Based Fluorophores with Molecular Design of Charge Transport and Red-Shifted Emission Proof. Journal of Materials Chemistry C, 2, 7188-7200.
http://dx.doi.org/10.1039/C4TC00876F
[15] Jo, W.J., Kim, K.H., No, H.C., Shin, D.-Y., Oh, S.J., Son, J.H., Kim, Y.H., Cho, Y.K., Zhao, Q.H., Lee, K.H., Oh, H.Y. and Kwon, S.K. (2009) High Efficient Organic Light Emitting Diodes Using New 9,10-Diphenylanthracene Derivatives Containing Bulky Substituents on 2,6-Positon. Synthetic Metals, 159, 1359-1364.
http://dx.doi.org/10.1016/j.synthmet.2009.03.007
[16] Kim, S.K., Yang, B., Ma, Y., Lee, J.H. and Park, J.W. (2008) Exceedingly Efficient Deep-Blue Electroluminescence from New Anthracenes Obtained Using Rational Molecular Design. Journal of Materials Chemistry C, 18, 3376-3384.
http://dx.doi.org/10.1039/b805062g
[17] Bin, J.K. and Hong, J.I. (2011) Efficient Blue Organic Light-Emitting Diode Using Anthracene-Derived Emitters Based on Polycyclic Aromatic Hydrocarbons. Organic Electronics, 12, 802-808.
http://dx.doi.org/10.1016/j.orgel.2011.02.011
[18] Ting, C.H. (1967) Electronic Structure and Intersystem Crossing in 9,10-Diphenylanthracene. Chemical Physics Letters, 1, 335-336.
http://dx.doi.org/10.1016/0009-2614(67)80010-1
[19] Park, J.W., Kim, Y.H., Jung, S.Y., Byeon, K.N. and Jang, S.H. (2008) Efficient and Stable Blue Organic Light-Emitting Diode Based on an Anthracene Derivative. Thin Solid Films, 516, 8381-8385.
http://dx.doi.org/10.1016/j.tsf.2008.04.080
[20] Chien, C.H., Chen, C.K., Hsu, F.M., Shu, C.F., Chou, P.T. and Lai, C.H. (2009) Multifunctional Deep-Blue Emitter Comprising an Anthracene Core and Terminal Triphenylphosphine Oxide Groups. Advanced Functional Materials, 19, 560-566.
http://dx.doi.org/10.1002/adfm.200801240
[21] Allen, A.D. and Cook, C.D. (1963) Substituted Phenylacetylenes. Infrared Spectra. Canadian Journal of Chemistry, 41, 1084-1087.
http://dx.doi.org/10.1139/v63-155
[22] Kukhta, A.V., Kukhta, I.N., Kukhta, N.A., Neyra, O.L. and Meza, E. (2008) DFT Study of the Electronic Structure of Anthracene Derivatives in Their Neutral, Anion and Cation Forms. Journal of Physics B: Atomic, Molecular and Optical Physics, 41, Article ID: 205701.
http://dx.doi.org/10.1088/0953-4075/41/20/205701
[23] Birks, J.B. (1975) Excimers. Reports on Progress in Physics, 38, 903-974.
http://dx.doi.org/10.1088/0034-4885/38/8/001
[24] Anthony, J.E. (2007) Induced π-Stacking in Acenes. In: Müller, T.J.J. and Bunz, U.H.F., Eds., Functional Organic Materials: Syntheses, Strategies and Applications, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 511-542.
http://dx.doi.org/10.1002/chin.200735267
[25] Lee, K.-S. (2002) Polymers for Photonics Applications I. Spring-Verlag Berlin Heidelberg, New York.
[26] Ullaa, H., Garudacharib, B., Satyanarayana, M.N., Umesha, G. and Isloorb, A.M. (2014) Blue Organic Light Emitting Materials: Synthesis and Characterization of Novel 1,8-Naphthalimide Derivatives. Optical Materials, 36, 704-711.
http://dx.doi.org/10.1016/j.optmat.2013.11.017.

  
comments powered by Disqus

Copyright © 2019 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.