PDI compounds have been studied, for example, in the context of sensitizers in solar cells,2 organic light-emitting diodes

(OLED),3 field-effect transistors,4 dyes,5 fluorescent labels6 (for instance for bio-imaging probes7), single-molecule spectroscopy,8 liquid crystals9 and supramolecular structures,10 for instance for transmembrane transport of ions.11
2 L. Schmidt-Mende, A. Fechtenko tter, K. Mu llen, E. Moons,R. H. Friend and J. D. MacKenzie, Science, 2001, 293, 11191122; J. J. Dittmer, E. A. Marseglia and R. H. Friend, Adv. Mater., 2000, 12, 12701274; J. J. Dittmer, R. Lazzaroni, P. Lecle` re, P. Moretti, M. Granstro m, K. Petritsch, E. A. Mareglia, R. H. Friend, J. L. Bredas, H. Rost and A. B. Holms, Sol. Energy Mater. Sol. Cells, 2000, 61, 5361; K. Petritsch, J. J. Dittmer, E. A. Marseglia, R. H. Friend, A. Lux, G. G. Rozenberg, P. Moretti and A. B. Holmes, Sol. Energy Mater. Sol. Cells, 2000, 61, 6372; S.-B. Rim, R. F. Fink, J. C. Scho neboom, P. Erk and P. Peumans, Appl. Phys. Lett., 2007, 91, 173504; S. Erten. F. Meghdadi, S. Gunes, R. Koeppe, N. S. Sariciftci and S. Icli, Eur. Phys. J.: Appl. Phys., 2006, 36, 225229; H. Qian, Z. Wang, W. Yue and D. Zhu, J. Am. Chem. Soc., 2007, 129, 1066410665; A. K. Pandey and J.-M. Nunzi, Appl. Phys. Lett., 2007, 90, 263508; Y. Ooyama and Y. Harima, Eur. J. Org. Chem., 2009, 29032934. 3 J. Qu, J. Zhang, A. C. Grimsdale, K. Mu llen, F. Jaiser, X. Yang and D. Neher, Macromolecules, 2004, 37, 82978306; X. Z. Jiang, Y. Q. Liu, S. G. Liu, W. F. Qiu, X. Q. Song and D. B. Zhu, Synth. Met., 1997, 91, 253256. 4 C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J.-L. Bredas, P. C. Ewbank and K. R. Mann, Chem. Mater., 2004, 16,44364451; Y. Sun, Y. Liu and D. Zhu, J. Mater. Chem., 2005, 15, 5365. 5 M. Green, in High Performance Pigments, ed. H. M. Smith, Wiley-VCH, Weinheim, 2002, pp. 249261; W. Herbst and K. Hunger, Industrial Organic Pigments, Wiley-VCH, Weinheim, 2004; H. Zollinger, Color Chemistry, Verlag Helvetica Chimica Acta, Zu rich, 2003. 6 M. C. Baier, J. Huber and S. Mecking, J. Am. Chem. Soc., 2009, 131, 1426714273 and references cited. 7 C. Kohl, T. Weil, J. Qu and K. Mu llen, Chem. Eur. J., 2004, 10, 52975310. 8 F. C. De Schryver, T. Vosch, M. Cotlet, M. van der Auweraer, K. Mu llen and J. Hofkens, Acc. Chem. Res., 2005, 38, 514522; M. Bendikov, F. Wudl and D. F. Perepichka, Chem. Rev., 2004, 104, 48914945; C. Flors, I. Oesterling, T. Schnitzler, E. Fron, G. Schweitzer, M. Sliwa, A. Herrmann, M. van der Auweraer, F. C. de Schryver, K. Mu llen and J. Hofkens, J. Phys. Chem. C, 2007, 111, 48614870; D. Wo ll, H. Uji-i, T. Schnitzler, J. Hotta, P. Dedecker, A. Herrmann, F. C. De Schryver, K. Mu llen and J. Hofkens, Angew. Chem., Int. Ed., 2008, 47, 783787. 9 Z. Chen, U. Baumeister, C. Tschierske and F. Wu rthner, Chem. Eur. J., 2007, 13, 450465; A. Wicklein, A. Lang, M. Muth and M. Thelakkat, J. Am. Chem. Soc., 2009, 131, 1444214453. 10 F. Wu rthner, Pure Appl. Chem., 2006, 78, 23412349; F. Wu rthner, Chem. Commun., 2004, 15641579; J. Baggerman, D. C. Jagesar,R. A. L. Valle e, J. Hofkens, F. C. De Schryver, F. Schelhase, F. Vo gtle and A. M. Brouver, Chem. Eur. J., 2007, 13, 12911299; J. Gebers, D. Rolland and H. Frauenrath, Angew. Chem., Int. Ed., 2009, 48, 44804483. 11 J. Mareda and S. Matile, Chem. Eur. J., 2009, 15, 2837.

For anti-counterfeit In recent years, many countries and companies research variety of anti-counterfeiting technology in order to combat fake and inferior products. Especially, more efforts are focused on the Bank notes and the anti-counterfeiting packaging of brand-name products. Thus demands promoted the research and development of the anti-counterfeiting technology. Photochromic materials, with special ink marker and high anti-counterfeiting features, have aroused extensive attention. Generally, there are three kinds of anti-counterfeiting technology: 1) visible without

fluorescence; 2) visible with significant fluorescence under ultraviolet light irradiation; 3) not visible with significant fluorescence under ultraviolet light irradiation. Organic photochromic compounds just as spiropyran and fulgide derivatives have been applied as anti-counterfeiting materials, they all belong to the second kind [1]. Diarylethene derivatives, the promising families of photochromic compounds, substituted with fluorescent chromophore, exhibit fluorescence modulation upon irradiation with ultraviolet and visible light [2e5]. The modulation of PDIs properties based on photochromic reactions has been studied [11e15]. Here we report on a reversible fluorescence modulation by photoinduced reaction with the diarylethene unit linking to the aromatic region of the perylene unit (Fig. 1).
Wenjuan Tan, Xin Li, Junji Zhang, He Tian*Dyes and Pigments 89 (2011) 260e265
[1] Guo J, Liu L, Liu G, Jia D, Xie X. Synthesis and solid-state photochromism of 1,3- diphenyl-4-(2-chlorobenzal)-5-hydroxypyrazole 4-methylthiosemicarbazone. Organic Letters 2007;9:3989e92. [2] Tian H, Yang S. Recent progresses on diarylethene based photochromic switches. Chemical Society Review 2004;33:85e97. [3] Norsten BT, Branda NR. Photoregulation of fluorescence in a porphyrinic dithienylethene photochrome. Journal of the American Chemical Society 2001;123:1784e5. [4] Tian H, Wang S. Photochromic bisthienylethene as multi-function switches. Chemical Communication; 2007:781e92. [5] Zhang J, Tan W, Meng X, Tian H. Soft-mimic gear-shift with a multi-stimulus modified diarylethene. Journal of Material Chemistry 2009;19:5726e9. [11] Fukaminato T, Irie M. Reversible fluorescence wavelength shift based on photoinduced aggregate formation. Advanced Materials 2006;18:3225 e8. [12] Zhu L, Wu W, Zhu MQ, Han JJ, Hurst JK, Li ADQ. Reversibly photoswitchable dual-color fluorescent nanoparticles as new tools for live-cell imaging. Journal of the American Chemical Society 2007;129:3524e6. [13] Fukaminato T, Umemoto T, Iwata Y, Yokojima S, Yoneyama M, Nakamura S, et al. Photochromism of diarylethene single molecules in polymer matrices. Journal of the American Chemical Society 2007;129:5932e8. [14] Berberich M, Krause AM, Orlandi M, Scandola F, Wrthner F. Toward fluorescent memories with nondestructive readout: photoswitching of fluorescence by intramolecular electron transfer in a diaryl ethene-perylene bisimide photochromic system. Angewandte Chemie International Edition 2008;47:6616e9. [15] Guo X, Zhang D, Zhu D. Logic control of the fluorescence of a new dyad, spiropyran-perylene diimide-spiropyran, with light, ferric ion, and proton: construction of a new three-input "AND" logic gate. Advanced Materials 2004;16:125e9.

Derivatives of perylene-3,4:9,10-bis(dicarboximide) (PDI) have attracted considerable attention due to their applications in molecular electronic devices, such as photovoltaic cells [1e8], light harvesting arrays [9,10], light-emitting diodes [11], organic fieldeffect transistors (OFETs) [12e17], photochromic materials [18], and LCD color filters [19]. These chromophores are advantageous due to their high photochemical stability, ease of synthetic modification and reversible redox properties. Moreover, the electronic characteristics of PDI can be fine-tuned by the substitution of the conjugated aromatic core.
[9] Li X, Sinks LE, Rybtchinski B, Wasielewski MR. Ultrafast aggregate-toaggregate energy transfer within self-assembled light-harvesting columns of zinc phthalocyanine tetrakis(perylenediimide). Journal of the American Chemical Society 2004;126:10810e1. [10] Rybtchinski B, Sinks LE, Wasielewski MR. Combining light-harvesting and charge separation in a self-assembled artificial photosynthetic system based on perylenediimide chromophores. Journal of the American Chemical Society 2004;126:12268e9. [11] Matsui M, Wang M, Funabiki K, Hayakawa Y, Kitaguchi T. Properties of novel perylene-3,4:9,10-tetracarboxidiimide-centred dendrimers and their application as emitters in organic electroluminescence devices. Dyes and Pigments 2007;74:169e75. [12] Wrthner F, Stolte M. Naphthalene and perylene diimides for organic transistors. Chemical Communications 2011;47:5109e15. [13] Reghu RR, Bisoyi HK, Grazulevicius JV, Anjukandi P, Gaidelis V, Jankauskas V. Air stable electron-transporting and ambipolar bay substituted perylene bisimides. Journal of Materials Chemistry 2011;21:7811e9. [14] Kim FS, Guo X, Watson MD, Jenekhe SA. High-mobility ambipolar transistors and high-gain inverters from a donor-acceptor copolymer semiconductor. Advanced Materials 2009;21:1e5. [15] Zaumseil J, Sirringhaus H. Electron and ambipolar transport in organic fieldeffect transistors. Chemical Reviews 2007;107:1296e323. [16] Locklin J, Li D, Mannsfeld SCB, Borkent EJ, Meng H, Advincula R, et al. Organic thin film transistors based on cyclohexyl-substituted organic semiconductors. Chemistry of Materials 2005;17:3366e74. [17] Jones BA, Ahrens MJ, Yoon MH, Facchetti A, Marks TJ, Wasielewski MR. Highmobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides). Angewandte Chemie International Edition 2004;43:6363e6. [18] Tan W, Li X, Zhang J, Tian H. A photochromic diarylethene dyad based on perylene diimide. Dyes and Pigments 2011;89:260 e5. [19] Sakong C, Kim YD, Choi JH, Yoon C, Kim JP. The synthesis of thermally-stable red dyes for LCD color filters and analysis of their aggregation and spectral properties. Dyes and Pigments 2011;88:166e73.