Soluble and stable near-infrared dyes based on polycyclic aromatics

Current Organic Chemistry

Volumn 14, Issue 18, 2010, Pages 2145-2168

  Jiao, Chongjun ^a   Wu, Jishan ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Near infrared dye; Phthalocyanine; Polycyclic aromatic hydrocarbon; Porphyrin; Rylene

Indexed keywords

ALKYLATION; AROMATIZATION; INFRARED ABSORPTION; POLYCYCLIC AROMATIC HYDROCARBONS; QUANTUM YIELD; VAT DYES;

CYANINE DYES; HIGH SOLUBILITY; NEAR-INFRARED ABSORPTION; NEAR-INFRARED DYES; PHOTO-STABILITY; PHTHALOCYANINE; PHYSICAL AND CHEMICAL PROPERTIES; POLYCYCLIC AROMATIC COMPOUNDS; POLYCYCLIC AROMATICS; RYLENE;

SOLUBILITY;

EID: 78649923848     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210793351616     Document Type: Article

References (77)

1. Kiyose, K.; Kojima, H.; Nagano, T. Functional near-infrared fluorescent probes. Chem. Asian J., 2008, 3, 506-515.
2. Amiot, C. L.; Xu, S. P.; Liang, S.; Pan, L. Y.; Zhao, X. J. Near-infrared fluorescent materials for sensing of biological target. Sensors, 2008, 8, 3082-3105.
3. Emmelius, M.; Pawlowski, G.; Vollmann, H.W. Materials for optical data storage. Angew. Chem., Int. Ed. Engl., 1989, 28, 1445-1470.
4. Kololuoma, T.; Oksanen, J.A.I.; Raerinne P.; Rantala, J.T. Dye-doped sol-gel coatings for near-infrared laser protection. J. Mater. Res., 2001, 16, 2186-2188.
5. Tani, T.; Kikuchi, S. Calculation of the electronic energy levels of various photographic sensitizing and desensitizing dyes in emulsions. Photogr. Sci. Eng., 1967, 11, 129-144.
6. Imahori, H.; Umeyama, T.; Ito, S. Large π-aromatic molecules as potential sensitizers for highly efficient dye-sensitized solar cells. Acc. Chem. Res., 2009, 42, 1809-1818.
7. Reddy, P. Y.; Gribabu, L.; Lyness, C.; Snaith, H. J.; Vijaykumar, C.; Chandrasekharam, M.; Lakshmikantam, M.; Yum, J.-H.; Kalyanasundaram, K.; Grätzel, M.; Nazeeruddin, M. K. Efficient sensitization of nanocrystalline TiO2 films by a near-IR absorbing unsymmetrical Zinc phthalocyanine. Angew. Chem., Int. Ed., 2007, 46, 373-376.
8. Beverina, L.; Fu, J.; Leclercq, A.; Zojer, E.; Pacher, P.; Barlow, S.; Van Stryland, E.W.; Hagan, D. J.; Brédas, J. -L.; Marder, S. R. Two-photon absorption at telecommunications wavelengths in a dipolar chromophore with a pyrrole auxiliary donor and thiazole auxiliary acceptor. J. Am. Chem. Soc., 2005, 127, 7282-7283.
9. Bouit, P. A.; Wetzel, G.; Berginc, G.; Loiseaux, B.; Toupet, L.; Feneyrou, P.; Bretonnière, Y.; Kamada, K.; Maury, O.; Andraud, C. Chem. Mater., 2007, 19, 5325-5335.
10. Gregory, P. High-Technology Applications of Organic Colorants, Plenum, New York, 1991.
11. Wu, J.; Pisula, W.; Müllen, K. Graphenes as potential material for electronics. Chem. Rev., 2007, 107, 718-747.
12. Wu, J. Polycyclic aromatic compounds for organic field-effect transistors: molecular design and syntheses. Curr. Org. Chem., 2007, 11, 1220-1240.
13. Fabian, J.; Nakanzumi, H.; Matsuoka, M. Near-infrared absorbing dyes. Chem. Rev., 1992, 92, 1197-1226.
14. Fischer, G. M.; Ehlers, A. P.; Zumbusch, A.; Daltrozzo, E. Near-infrared dyes and fluorophores based on diketopyrrolopyrroles. Angew. Chem., Int. Ed., 2007, 46, 3750-3753.
15. Zhao, W.; Carreira, E. M. Conformationally restricted aza-Bodipy: a highly fluorescent, stable, near-infrared-absorbing dye. Angew. Chem., Int. Ed., 2005, 44, 1677-1679.
16. Tian, M.; Tatsuura, S.; Furuki, M.; Sato, Y.; Iwasa, I.; Pu, L. S. Discovery of novel dyes with absorption maxima at 1.1 μm. J. Am. Chem. Soc., 2003, 125, 348-349.
17. Nagao, Y. Synthesis and properties of perylene pigments. Prog. Org. Coatings, 1997, 31, 43-49.
18. Gade, L. H.; Galka, C.H.H.; Hellmann, K. W.; Williams, R. M.; de Cola, L.; Scowen, I. J.; McMartin, M. Tetraaminoperylenes: their efficient synthesis and physical properties. Chem. Eur. J., 2002, 8, 3732-3746.
19. Lang, E.; Würthner, F.; Kohler, J. Photophysical properties of a tetraphenoxy- substituted perylene bisimide derivative characterized by singlemolecule spectroscopy. ChemPhysChem., 2005, 6, 935-941.
20. Cremer, J.; Bäuerle, P. Perylene-oligothiophene-perylene triads for photovoltaic applications. Eur. J. Org. Chem., 2005, 3715-3723.
21. Avlasevich, Y.; Kohl, C.; Müllen, K. Facile synthesis of terrylene and its isomer benzoindenoperylene. J. Mater. Chem., 2006, 16, 1053-1057.
22. Bohnen, A.; Koch, K. H.; Lüttke, W.; Müllen, K. Oligorylene as a model for "poly(perinaphtha1ene)". Angew. Chem., Int. Ed., 1990, 29, 525-527.
23. Hortrup, F. O.; Müller, G. R. J.; Quante, H.; de Feyter, S.; de Schryver, F. C.; Müllen, K. Terrylenimides: new NIR fluorescent dyes. Chem. Eur. J., 1997, 3, 219-225.
24. Nolde, F.; Qu, J.; Kohl, C.; Pschirer, N. G.; Reuther, E.; Müllen, K. Synthesis and modification of terrylenediimides as high-performance fluorescent dyes. Chem. Eur. J., 2005, 11, 3959-3967.
25. Quante, H.; Müllen, K. Quaterrylenebis(dicarboximides). Angew. Chem., Int. Ed. Engl., 1995, 34, 1323-1325.
26. Langhals, H.; Schönmann, G.; Feiler, L. A two-step synthesis of quaterrylenetetracarboxylic bisimides-novel NIR fluorescent dyes. Tetrahedron Letters, 1995, 36, 6423-6424.
27. Geerts, Y.; Quante, H.; Platz, H.; Mahrt, R.; Hopmeier, M.; Böhm, A.; Müllen, K. Quaterrylenebis(dicarboximide)s: near infrared absorbing and emitting dyes. J. Mater. Chem., 1998, 8, 2357-2369.
28. Langhals, H.; Büttner, J.; Blanke, P. A two-step synthesis of quarterrylene bisimides: application of the 'green route' method. Synthesis, 2005, 364-366.
29. Tam-Chang, S. W.; Seo, W.; Iverson, I. K. Synthesis and studies of the properties of a liquid-crystalline quaterrylenebis(dicarboximide) by 1H NMR and UV-vis spectroscopies. J. Org. Chem., 2004, 69, 2719-2723.
30. Tam-Chang, S. W.; Seo, W.; Iverson, I. K.; Casey, S. M. Ionic quaterrylenebis(dicarboximide): a novel mesogen and long-wavelength polarizing material. Angew. Chem., Int. Ed., 2003, 42, 897-900.
31. Nolde, F.; Pisula, W.; Müller, S.; Kohl, C.; Müllen, K. Synthesis and selforganization of core-extended perylene tetracarboxdiimides with branched alkyl substituents. Chem. Mater., 2006, 18, 3715-3725.
32. Jiao, C.; Huang, K.; Luo, J.; Zhang, K.; Chi, C.; Wu, J. Bis-N-annulated quaterrylenebis(dicarboximide) as a new soluble and stable near-infrared dye. Org. Lett., 2009, 11, 4505-4511.
33. Jiang, W.; Qian, H; Li, Y.; Wang, Z. Heteroatom-annulated perylenes: practical synthesis, photophysical properties, and solid-state packing arrangement. J. Org. Chem., 2008, 73, 7369-7372.
34. Avlasevich, Y.; Müller, S.; Erk, P.; Müllen, K. Novel core-expanded rylenebis(dicarboximide) dyes bearing pentacene units: facile synthesis and photophysical properties. Chem. Eur. J., 2007, 13, 6555-6561.
35. Liu, Z.; Zhang, X.; Larock, R. C. Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls. J. Am. Chem. Soc., 2005, 127, 15716-15717.
36. Avlasevich, Y.; Müllen, K. An efficient synthesis of quaterrylenedicarboximide NIR dyes. J. Org. Chem., 2007, 72, 10243-10246.
37. Pschirer, N. G.; Kohl, C.; Nolde, F.; Qu, J.; Müllen, K. Pentarylene- and hexarylenebis(dicarboximide)s: near-infrared-absorbing polyaromatic dyes. Angew. Chem.Int. Ed., 2006, 45, 1401-1404.
38. Avlasevich, Y.; Müllen, K. Dibenzopentarylenebis(dicarboximide)s: novel near-infrared absorbing dyes. Chem. Commun., 2006, 4440-4442.
39. Adachi, M.; Nagao, Y. Design of near-infrared dyes based on π-conjugation system extension 2.theoretical elucidation of framework extended derivatives of perylene chromophore. Chem. Mater., 2001, 13, 662-669.
40. Zhao, Y.; Ren, A.-M.; Feng, J.-K.; Sun, C.-C. Theoretical study of onephoton and two-photon absorption properties of perylene tetracarboxylic derivatives. J. Chem. Phys., 2008, 129, 014301.
41. Désilets, D.; Kazmaier, P. M.; Burt, R. A.; Hamer, G. K. Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthracene green and derivatives. Can. J. Chem., 1995, 73, 325-335.
42. Yao, J.; Chi, C.; Wu, J.; Loh, K. Bisanthracene bis(dicarboxylic imide)s as soluble and stable NIR dyes. Chem. Eur. J., 2009, 15, 9299-9302.
43. Arabei, S. M.; Pavich, T. A. Spectral-luminescent properties and photoinduced transformations of bisanthene and bisanthenequinone. J. Appl. Spectr., 2000, 67, 236-244.
44. Kuroda, H.; Flood, E. A. Effect of oxygen on semiconductivity of mesonaphthodianthrene and mesonaphthodianthrone. J. Chem. Phys., 1960, 33, 952-953.
45. Clar, E. Aromatic hydrocarbons XLII. The condensation principle, a simple new principle in the structure of aromatic hydrocarbon. Chem. Ber., 1948, 81, 52-63.
46. Li, J.; Zhang, K.; Zhang, X.; Huang, K.; Chi, C.; Wu, J. Meso-substituted bisanthenes as soluble and stable near-infrared dyes. J. Org. Chem., 2010, 95, 856-863.
47. Qian, H.; Negri, F.; Wang, C.; Wang, Z. Fully conjugated tri(perylene bisimides): an approach to the construction of n-type graphene nanoribbons. J. Am. Chem. Soc., 2005, 130, 17970-17976.
48. Langhals, H.; Blanke, P. An approach to novel NIR dyes utilising π-effect donor groups. Dyes Pigm., 2003, 59, 109-116.
49. Albinsson, B.; Eng, M.P.; Pettersson, K.; Winters, M.U. Electron and energy transfer in donor-acceptor systems with conjugated molecular bridges. Phys. Chem. Chem. Phys., 2007, 9, 5847-5864
50. Li, C.; Schöneboom, J.; Liu, Z.; Erk, P.; Herrmann, A.; Müllen, K. Rainbow perylene monoimides: easy control of optical properties. Chem. Eur. J., 2009, 15, 878-884.
51. Kohl, C.; Becker, S.; Müllen, K. Bis(rylenedicarboximide)-a,d-1,5- diaminoanthraquinones as unique infrared absorbing dyes. Chem. Commun., 2002, 2778-2779.
52. Zhang, K.; Huang, K.; Li, J.; Luo, J.; Chi, C.; Wu, J. A soluble and stable quinoidal bisanthene with NIR absorption and amphoteric redox behavior. Org. Lett., 2009, 11, 4854-4857.
53. Liu, Z.; Li, C.; Wagner, M.; Avlasevich, Y.; Herrmann, A.; Müllen, K. Amino-substituted rylene dicarboximides and their quinoidal charge delocalization after deprotonation. Chem. Commun., 2008, 5028-5030.
54. Kim, H. M.; Cho, B. R. Two-photon materials with large two-photon cross sections. Structure-property relationship. Chem. Commun., 2009, 153-164.
55. Aratani, N.; Kim, D.; Osuka, A. π-Conjugation enlargement toward the creation of multi-porphyrinic systems with large two-photon absorption properties. Chem. Asian J., 2009, 4, 1172-1182.
56. Tsuda, A.; Nakano, A.; Furuta, H.; Yamochi, H.; Osuka, A. Doubly meso-π- linked diporphyrins from oxidation of 5,10,15-triaryl-Substituted NiII-and PdII- porphyrins. Angew. Chem. Int. Ed., 2000, 39, 558-561.
57. Tsuda, A.; Nakamura, Y.; Osuka, A. Synthesis of meso-π doubly linked porphyrin tapes. Chem. Commun., 2003, 1096-1097.
58. Yoon, M. C.; Noh, S. B.; Tsuda, A.; Nakamura, Y.; Osuka, A.; Kim, D. Photophysics of meso-π doubly linked Ni(II) porphyrin arrays: large twophoton absorption cross-section and fast energy relaxation dynamics. J. Am. Chem. Soc., 2007, 129, 10080-10081.
59. Ikeda, T.; Aratani, N.; Easwaramoorthi, S.; Kim, D.; Osuka, A. Meso-π doubly linked Zn(II) porphyrin trimers: distinct anti-versus-syn effects on their photophysical properties. Org. Lett., 2009, 11, 3080-3083.
60. Tsuda, A.; Furuta, H.; Osuka, A. Completely fused diporphyrins and triporphyrins. Angew. Chem. Int. Ed., 2000, 39, 2549-2552.
61. Tsuda, A.; Furuta, H.; Osuka, A. Syntheses, structural characterizations, and optical and electrochemical properties of directly fused diporphyrins. J. Am. Chem. Soc., 2001, 123, 10304-10321.
62. Tsuda, A.; Osuka, A. Fully conjugated porphyrin tapes with electronic absorption bands that reach into infrared. Science, 2001, 293, 79-82.
63. Ikeda, T.; Lintuluoto, J. M.; Aratani, N.; Yoon, Z. S.; Kim, D; Osuka, A. Synthesis of doubly strapped meso-meso-linked porphyrin arrays and triply linked conjugated porphyrin tapes. Eur. J. Org. Chem., 2006, 3193-3204.
64. Nakamura, Y.; Jang, S. Y.; Tanaka, T.; Aratani, N; Lim, J. M.; Kim, K. S.; Kim, D.; Osuka, A. Two-dimensionally extended porphyrin tapes: synthesis and shape-dependent two-photon absorption properties. Chem. Eur. J., 2008, 14, 8279-8289.
65. Nakamura, Y.; Hwang, I.-W.; Aratani, N.; Ahn, T. K.; Ko, D. M.; Takagi, A.; Kawai, T.; Matsumoto, T.; Kim, D.; Osuka, A. Directly meso-meso linked porphyrin rings: synthesis, characterization, and efficient excitation energy hopping. J. Am. Chem. Soc., 2005, 127, 236-246.
66. Nakamura, Y.; Aratani, N.; Shinokubo, H.; Takagi, A.; Kawai, T.; Matsumoto, T. Yoon, Z. S.; Kim, D. Y.; Ahn, T. K.; Kim, D.; Muranaka, A.; Kobayashi, N.; Osuka, A. A directly fused tetrameric porphyrin sheet and its anomalous electronic properties that arise from the planar cyclooctatetraene core. J. Am. Chem. Soc., 2006, 128, 4119-4127.
67. Tanaka, M.; Hayashi, S.; Eu, S.; Umeyama, T.; Matano, Y.; Imahori, H. Novel unsymmetrically π-elongated porphyrin for dye-sensitized TiO2 cells. Chem. Commun., 2007, 2069-2071.
68. Yamane, O.; Sugiura, K.; Miyasaka, H.; Nakamura, K.; Fujimoto, T.; Nakamura, K.; Kaneda, T.; Sakata, Y.; Yamashita, M. Pyrene-fused porphyrins: annulation reactions of meso-pyrenylporphyrins. Chem. Lett., 2004, 33, 40-41.
69. Davis, N. K. S.; Pawlicki, M.; Anderson, Harry L. Expanding the porphyrin π-System by fusion with anthracene. Org. Lett., 2008, 10, 3945-3947.
70. Kurotobi, K.; Kim, K. S.; Noh, S. B.; Kim, D.; Osuka, A. A quadruply azulene- fused porphyrin with intense Near-IR absorption and a large twophoton absorption cross section. Angew. Chem. Int. Ed., 2006, 45, 3944-3947.
71. Gill, H. S.; Marmjanz, M.; Santamaría, J.; Finger, I.; Scott, M. J. Facile oxidative rearrangement of dispiro-porphodimethenes to nonplanar and sheetlike porphyrins with intense absorptions in the Near-IR region. Angew. Chem., Int. Ed., 2004, 43, 485-490.
72. Bedworth, P.V.; Perry, J. W.; Marder, S. R. The synthesis of a symmetrically substituted a-octa(isopentoxy)anthralocyanine. Chem. Commun., 1997, 1353-1354.
73. Hohr, B.; Wegner, G.; Ohta, K. Synthesis of triphenylene-based porphyrazinato metal(II) complexes which display discotic columnar mesomorphism. J. Chem. Soc., Chem. Commun., 1995, 995-996.
74. Cammidge, A. N.; Gopee, H. Macrodiscotic triphenylenophthalocyanines. Chem. Commun., 2002, 966-967.
75. Sooksimuang, T.; Mandal, B. K. [5]Helicene-fused phthalocyanine derivatives. New members of the phthalocyanine family. J. Org. Chem., 2003, 68, 652-655.
76. Cammidge, A. N.; Gopee, H. Perylenophthalocyanines. Chem. Eur. J., 2006, 12, 8609-8613.
77. Fogel, Y.; Kastler, M.; Wang, Z.; Andrienko, D.; Bodwelland, G. J.; Müllen, K. Electron-deficient N-heteroaromatic linkers for the elaboration of large, soluble polycyclic aromatic hydrocarbons and their use in the synthesis of some very large transition metal complexes. J. Am. Chem. Soc., 2007, 129, 11743-11749.