Thiomethyl Derivatives of Two Oligo(p-phenylene vinylenes) as New Aggregation-Induced Piezofluorochromic Emitters

DOI: 10.4236/msa.2013.46043   PDF   HTML   XML   3,594 Downloads   5,395 Views   Citations


Two piezochromic fluorescent compounds are prepared by introducing thiomethyl substituents to the peripheralpositions of two related cyano oligo(p-phenylene vinylenes) (CN-OPV). The new derivatives, namely, 1,4-bis[2-cyano-2(4-thiomethylphenyl)ethenyl]benzene (TOPV1) and 1,4-bis(1-cyano-2-(4-thiomethylphenyl)ethenyl) benzene (TOPV2), are characterized by NMR, powder X-ray diffraction data (XRD) and differential scanning calorimetric (DSC) data. UV-Vis and fluorescence spectra are also measured. TOPV1 with the cyano groups farther away from the central aromatic ring is photoluminescent, and on application of pressure exhibits a more obvious color change and higher Stokes shift than those measured for TOPV2. We also observe piezochromic aggregation-induced emission (PAIE) for TOPV2, but TOPV1 does not exhibit any PAIE.

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X. Hou, J. Ling, N. Arulsamy and J. Huo, "Thiomethyl Derivatives of Two Oligo(p-phenylene vinylenes) as New Aggregation-Induced Piezofluorochromic Emitters," Materials Sciences and Applications, Vol. 4 No. 6, 2013, pp. 331-336. doi: 10.4236/msa.2013.46043.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] D. A. Davis, A. Hamilton, J. Yang, J. S. Moore and N. R. Sottos, “Force-Induced Activation of Covalent Bonds in Mechanoresponsive Polymeric Materials,” Nature, Vol. 459, No. 3, 2009, pp. 68-72. doi:10.1038/nature07970
[2] J. W. Chung, Y. You, H. S. Huh, B. K. An, S. J. Yoon, S. H. Kim, S. W. Lee and S. Park, “Shearand UV-Induced Fluorescence Switching in Stilbenic π-Dimer Crystals Powered by Reversible [2 + 2] Cycloaddition,” Journal of the American Chemical Society, Vol. 131, No. 23, 2009, pp. 8163-8172. doi:10.1021/ja900803d
[3] Y. Sagara, T. Mutai, I. Yoshikawa and K. Araki, “Material Design for Piezochromic Luminescence: HydrogenBond-Directed Assemblies of a Pyrene Derivative,” Journal of the American Chemical Society, Vol. 129, No. 6, 2007, p. 1520. doi:10.1021/ja0677362
[4] Y. Muramatsu, T. Yamamoto, M. Hasegawa, T. Yagi and H. Koinuma, “Piezochromic Behaviour of Regioregular Poly(3-hexylthiophene-2,5-diyl) and Poly(5,8-dihexadecyloxyanthraquinone-1,4-diyl),” Polymer, Vol. 42, No. 15, 2001, pp. 6673-6675. doi:10.1016/S0032-3861(01)00136-7
[5] Y. Dong, J. W. Y. Lam, A. Qin, J. Liu, Z. Li, B. Z. Tang, J. Sun and H. S. Kwok, “Aggregation-Induced Emissions of Tetraphenylethene Derivatives and Their Utilities as Chemical Vapor Sensors and in Organic Light-Emitting Diodes,” Applied Physics Letters, Vol. 91, No.1, 2007, Article ID: 011111. doi:10.1063/1.2753723
[6] Z. Ning, Z. Chen, Q. Zhang, Y. Yan, S. Qian, Y. Cao and H. Tian, “Aggregation-Induced Emission (AIE)-Active Starburst Triarylamine Fluorophores as Potential NonDoped Red Emitters for Organic Light-Emitting Diodes and Cl2 Gas Chemodosimeter,” Advanced Functional Materials, Vol. 17, No. 18, 2007, pp. 3799-3807. doi:10.1002/adfm.200700649
[7] B. R. Crenshaw, M. Burnworth, D. Khariwala, A. Hiltner, P. T. Mather, R. Simha and C. Weder, “Deformation-Induced Color Changes in Mechanochromic Polyethylene Blends,” Macromolecules, Vol. 40, No. 7, 2007, pp. 2400-2048. doi:10.1021/ma062936j
[8] M. Kinami, B. R. Crenshaw and C. Weder, “Polyesters with Built-In Threshold Temperature and Deformation Sensors,” Chemistry of Materials, Vol. 18, No. 4, 2006, pp. 946-955. doi:10.1021/cm052186c
[9] S. J. Toal, K. A. Jones, D. Magde and W. C. Trogler, “Luminescent Silole Nanoparticles as Chemoselective Sensors for Cr(VI),” Journal of the American Chemical Society, Vol. 127, No. 33, 2005, pp. 11661-11665. doi:10.1021/ja052582w
[10] S. Hirata and T. Watanabe, “Reversible Thermoresponsive Recording of Fluorescent Images (TRF),” Advanced Materials, Vol. 18, No. 20, 2006, pp. 2725-2729. doi:10.1002/adma.200600209
[11] S. J. Lim, B. K. An, S. D. Jung, M. A. Chung and S. Y. Park, “Photoswitchable Organic Nanoparticles and a Polymer Film Employing Multifunctional Molecules with Enhanced Fluorescence Emission and Bistable Photochromism,” Angewandte Chemie International Edition, Vol. 43, No. 46, 2004, pp. 6346-6350. doi:10.1002/anie.200461172
[12] M. Irie, T. Fukaminato, T. Sasaki, N. Tamai and T. Kawai, “Organic Chemistry: A Digital Fluorescent Molecular Photoswitch,” Nature, Vol. 420, No. 6917, 2002, pp. 759-760. doi:10.1038/420759a
[13] G. S. Papaefstathiou, Z. Zhong, L. Geng and L. R. MacGillivray, “Coordination-Driven Self-Assembly Directs a Single-Crystal-to-Single-Crystal Transformation That Exhibits Photocontrolled Fluorescence,” Journal of the American Chemical Society, Vol. 126, No. 30, 2004, pp. 9158-9159. doi:10.1021/ja047819n
[14] A. Kishimura, T. Yamashita, K. Yamaguchi and T. Aida, “Rewritable Phosphorescent Paper by the Control of Competing Kinetic and Thermodynamic Self-Assembling Events,” Nature Materials, Vol. 4, No. 1, 2005, pp. 546-549. doi:10.1038/nmat1401
[15] Z. Chi, X. Zhang, B. Xu, X. Zhou, C. Ma, Y. Zhang, S. Liu and J. Xu, “Recent Advances in Organic Mechanofluorochromic Materials,” Chemical Society Reviews, Vol. 41, No. 10, 2012, pp. 3878-3896. doi:10.1039/c2cs35016e
[16] S. Mizukami, H. Hojou, K. Sugaya, E. Koyama, H. Tokuhisa, T. Sasaki and M. Kanesato, “Fluorescence Color Modulation by Intramolecular and Intermolecular π-π Interactions in a Helical Zinc(II) Complex,” Chemistry of Materials, Vol. 17, No. 1, 2005, pp. 50-56. doi:10.1021/cm049744s
[17] C. Lowe and C. Weder, “Oligo(p-phenylene vinylene) Excimers as Molecular Probes: Deformation-Induced Color Changes in Photoluminescent Polymer Blends,” Advanced Materials, Vol. 14, No. 22, 2002, pp. 1625-1629. doi:10.1002/1521-4095(20021118)14:22<1625::AID-ADMA1625>3.0.CO;2-Q
[18] J. Kunzelman, M. Kinami, B. R. Crenshaw, J. D. Protasiewicz and C. Weder, “Oligo(p-phenylene vinylene)s as a ‘New’ Class of Piezochromic Fluorophores,” Advanced Materials, Vol. 20, No. 1, 2008, pp. 119-122. doi:10.1002/adma.200701772
[19] C. Lowe and C. Weder, “Synthesis and Properties of Photoluminescent 1,4-Bis-(α-cyano-4-methoxystyryl)benzenes,” Synthesis, Vol. 9, No. 9, 2002, pp. 1185-1190. doi:10.1055/s-2002-32537
[20] M. A. Garcia-Garibay, “Molecular Crystals on the Move: From Single-Crystal-to-Single-Crystal Photoreactions to Molecular Machinery,” Angewandte Chemie International Edition, Vol. 46, No. 47, 2007, pp. 8945-8947. doi:10.1002/anie.200702443
[21] B.-K. An, S. K. Kwon, S. D. Jung and S. Y. Park, “Enhanced Emission and Its Switching in Fluorescent Organic Nanoparticles,” Journal of the American Chemical Society, Vol. 124, No. 48, 2002, pp. 14410-14415. doi:10.1021/ja0269082

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