Reactive bay functionalized perylene monoimide-polyhedral oligomeric silsesquioxane organic electronic dye

• Autorzy: Wangatia L. M. , Sun B. , Zeng T. , Zhu M.

Identyfikatory

DOI

10.1515/msp-2015-0016

• Języki publikacji: EN

Abstrakty

EN

Aggregation-induced quenching is particularly detrimental in perylene diimides, which are characterized by a near-unity fluorescence quantum yield in solution but are far less emissive in the solid state. Previously, perylene diimide has been improved by linking it to the inorganic cage of polyhedral oligomeric silsesquioxanes. As a further study on perylene diimidepolyhedral oligomeric silsesquioxanes, we report on a double functionalized molecular structure, which can be used for substitution at the bay area and as a side group in other materials. Typical solution absorption and emission features of the perylene diimide fragment have been observed in this new reactive perylene diimide-polyhedral oligomeric silsesquioxane. Moreover, reduced stacking during aggregation and spherical particles exhibiting solid fluorescence have been obtained. Organic semiconducting material with enhanced solid state photophysical properties, like solid fluorescence is a subject of great interest owing to its possible high-tech applications in optoelectronic devices.

Słowa kluczowe

EN

perylene diimides; polyhedral oligomeric silsesquioxane; fluorescence; optoelectronics; self assembly

• Wydawca: De Gruyter
• Czasopismo: Materials Science Poland
• Rocznik: 2015
• Tom: Vol. 33, No. 1
• Strony: 113--121
• Opis fizyczny: Bibliogr. 42 poz., rys.

Twórcy

autor

Wangatia L. M.

• State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, P. R. China

autor

Sun B.

• State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, P. R. China

autor

Zeng T.

• State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, P. R. China

autor

Zhu M.

• State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University, Shanghai 201620, P. R. China

Bibliografia

• [1] ANTHONY J.E., EATON D.L., PARKIN S.R., Org. Lett., 4 (2002), 15.
• [2] HOROWITZ G., Adv. Mater., 10 (1998), 365.
• [3] PAYNE M.M., DELCAMP J.H., PARKIN S.R., ANTHONY J.E., Org. Lett., 6 (2004), 1609.
• [4] GREGG B.A., FOX M.A., BARD A.J., J. Phys. Chem., 94 (1990), 1586.
• [5] HOROWITZ G., KOUKI F., SPEARMAN P., FICHOU D., NOGUES C., PAN X., GARNIER F., Adv. Mater., 8 (1996), 242.
• [6] CHESTERFIELD R., MCKEEN J.C., NEWMAN C.R., EWBANK P.C., DA SILVA FILHO D.A., BREDAS J.- L., MILLER L.L., MANN K.R., FRISBIE C.D., J. Phys. Chem. B, 108 (2004), 19281.
• [7] JONES B.A., AHRENS M.J., YOON M.H., FACCHETTI A., MARKS T.J., WASIELEWSKI M.R., Angew. Chem. Int. Edit., 116 (2004), 6523.
• [8] SCHMIDT-MENDE L., FECHTENKOTTER A., MULLEN K., MOONS E., FRIEND R.H., MACKENZIE J., Science, 293 (2001), 1119.
• [9] GREGG B.A., J. Phys. Chem. B, 107 (2003), 4688.
• [10] GREGG B.A., J. Phys. Chem., 100 (1996), 852.
• [11] LIU Y., XIAO S., LI H., LI Y., LIU H., LU F., ZHUANG J., ZHU D., J. Phys. Chem. B, 108 (2004), 6256.
• [12] TAMIZHMANI G., DODELET J., COTE R., GRAVEL D., Chem. Mater., 3 (1991), 1046.
• [13] PEETERS E., VAN HAL P.A., MESKERS S.C., JANSSEN R.A., MEIJER E., Chem.-Eur. J., 8 (2002), 4470.
• [14] STUIJK C.W., SIEVAL A.B., DAKHORST J.E., VAN DIJK M., KIMKES P., KOEHORST R.B., DONKER H., SCHAAFSMA T.J., PICKEN S.J., VAN DE CRAATS A.M., J. Am. Chem. Soc., 122 (2000), 11057.
• [15] ROHR U., SCHLICHTING P., BOHM A., GROSS M., MEERHOLZ K., BRAUCHLE C., MULLEN K., Angew. Chem. Int. Edit., 37 (1998), 1434.
• [16] ALIBERT-FOUET S., DARDEL S., BOCK H., OUKACHMIH M., ARCHAMBEAU S., SEGUY I., JOLINAT P., DESTRUEL P., ChemPhysChem., 4 (2003), 983.
• [17] SCHOUWINK P., SCHAFER A., SEIDEL C., FUCHS H., Thin Solid Films, 372 (2000), 163.
• [18] RANKE P., BLEYL I., SIMMERER J., HAARER D., BACHER A., SCHIMIDT H., Appl. Phys. Lett., 71 (1997), 1332.
• [19] ZUKAWA T., NAKA S., OKADA H., ONNAGAWA H., J. App. Phys., 91 (2002), 1171.
• [20] ZANG L., LIU R., HOLMAN M.W., NGUYEN K.T., ADAMS D.M., J. Am. Chem. Soc., 124 (2002), 10640.
• [21] COLACIO E., DOMINGUEZ-VERA J.M., LLORET F., MORENO-SANCHEZ J.M., KIVEKAS R., RODRIGUEZ A., SILLANPAA R., Inorg. Chem., 42 (2003), 4209.
• [22] LIU R., HOLMAN M.W., ZANG L., ADAMS D.M., J. Phys. Chem. A, 107 (2003), 6522.
• [23] HOLMAN M.W., LIU R., ZANG L., YAN P., DIBENEDETTOS A., BOWER R.D., ADAMS D.M., J. Am. Chem. Soc., 126 (2004), 16126.
• [24] SAUER M., Angew. Chem. Int. Edit., 42 (2003), 1790.
• [25] GRIMSDALE A.C., MULLEN K., Angew. Chem. Int. Edit., 44 (2005), 5592.
• [26] XU B., XIAO X., YANG X., ZANG L., TAO N., J. Am. Chem. Soc., 127 (2005), 2386.
• [27] LI X., XU B., XIAO X., YANG X., ZANG L., TAO N., Faraday Discuss., 131 (2006), 111.
• [28] NEWMAN C.R., FRISBIE C.D., DA SILVA FILHO D.A., BREDAS J.-L., EWBANK P.C., MANN K.R., Chem. Mater., 16 (2004), 4436.
• [29] HUANG C., BARLOW S., MARDER S.R., J. Org. Chem., 76 (2011), 2386.
• [30] LANGHALS H., Helv. Chim. Acta, 88 (2005), 1309.
• [31] XU H., KUO S.-W., LEE J.-S., CHANG F.-C., Macromolecules, 35 (2002), 8788.
• [32] DEVAUX E., ROCHERY M., BOURBIGOT S., Fire Mater., 26 (2002), 149.
• [33] LEU C.-M., CHANG Y.-T., WEI K.-H., Macromolecules, 36 (2003), 9122.
• [34] ZHANG W., MULLER A.H., Prog. Polym. Sci., 38 (2013), 1121.
• [35] REN X., SUN B., TSAI C.-C., TU Y., LENG S., LI K., KANG Z., HORN R.M.V., LI X., ZHU M., J. Phys. Chem. B, 114 (2010), 4802.
• [36] ZHUANG X.-D., CHEN Y., ZHANG B., LI Y., YU B., QIAO W., New. J. Chem., 34 (2010), 1120.
• [37] LUCENTI E., BOTTA C., CARIATI E., RIGHETTO S., SCARPELLINI M., TORDIN E., UGO R., Dyes Pigments, 96 (2013), 748.
• [38] B¨OHM A., ARMS H., HENNING G., BLASCHKA P., (BASF AG) German Pat. DE 19547209 A1, 1997, in Chem. Abstr., 127 (1997), p. 96569g.
• [39] WU S., HAYAKAWA T., KIKUCHI R., GRUNZINGER S.J., KAKIMOTO M.-A., OIKAWA H., Macromolecules, 40 (2007), 5698.
• [40] SUN H.-J., TU Y., WANG C.-L., VAN HORN R.M., TSAI C.-C., GRAHAM M.J., SUN B., LOTZ B., ZHANG W.-B., CHENG S.Z., J. Mater. Chem., 21 (2011), 14240.
• [41] ASIR S., DEMIR A.S., ICIL H., Dyes Pigments, 84 (2010), 1.
• [42] GOERL D., ZHANG X., WURTHNER F., Angew. Chem. Int. Edit., 51 (2012), 6328.