Synthesis and optical properties of triphenylene-based conjugated dendrons

Tetrahedron

Volumn 65, Issue 7, 2009, Pages 1247-1256

  Bagui, Mahuya ^a   Melinger, Joseph S ^b   Chakraborty, Sanjiban ^a   Keightley, J Andrew ^a   Peng, Zhonghua ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

Dendrimers; Fluorescence; Light harvesting; Triphenylene

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON; TRIPHENYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; DENDRITE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; SOLID STATE; SPECTRAL SENSITIVITY; SYNTHESIS;

EID: 58149334779     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.017     Document Type: Article

References (67)

1. Newkome G.R., Moorefield C.N., and Vögtle F. Dendritic Molecules: Concepts, Syntheses, Perspectives (1996), VCH, Weinheim
2. Fréchet J.M.J., and Hawker C.J. Synthesis and Properties of Dendrimers and Hyperbranched Polymers. 2nd Supplement. In: Aggarwal S.L., and Russo S. (Eds). Comprehensive Polymer Science (1996), Pergamon, Oxford
3. Fischer M., and Vögtle F. Angew. Chem., Int. Ed. 38 (1999) 884
4. Smith D.K., and Diederich F. Chem.-Eur. J. 4 (1998) 1353
5. Tomalia D.A., Naylor A.M., and Goddart III W.A. Angew. Chem., Int. Ed. Engl. 29 (1990) 138
6. Zeng F., and Zimmerman S.C. Chem. Rev. 97 (1997) 1681
7. Bar-Haim A., Klafter J., and Kopelman R. J. Am. Chem. Soc. 119 (1997) 6197
8. Li W., Jong W., and Aida T. Macromol. Eng. 2 (2007) 1057
9. Lo S.C., and Burn P.L. Chem. Rev. 107 (2007) 1097
10. Nantalaksakul A., Reddy D.R., Bardeen C.J., and Thayumanavan S. Photosynth. Res. 87 (2006) 133
11. D'Ambruoso G.D., and McGrath D.V. In: Andrews D.L. (Ed). Energy Harvesting Materials (2005), World Scientific, Singapore p 281
12. Flomenbom O., Klafter J., Amir R.J., and Shabat D. In: Andrews D.L. (Ed). Energy Harvesting Materials (2005), World Scientific, Singapore p 245
13. Devadoss C., Bharathi P., and Moore J.S. J. Am. Chem. Soc. 118 (1996) 9635
14. Kopidakis N., Mitchell W.J., van de Lagemaat J., Ginley D.S., Rumbles G., Shaheen S.E., and Rance W.L. Appl. Phys. Lett. 89 (2006) 103524
15. Meskers S.C.J., Bender M., Hubner J., Romanovskii Y.V., Oestreich M., Schenning A.P.H.J., Meijer E.W., and Bassler H. J. Phys. Chem. A 105 (2001) 10220
16. Lu D., Feyter S.D., Cotlet M., Stefan A., Wiesler U.M., Herrman A., Grebel-Koehler D., Qu J., Mullen K., and Schryver F.C.D. Macromolecules 36 (2003) 5918
17. Gilat S.L., Adronov A., and Fréchet J.M.J. Angew. Chem., Int. Ed. 38 (1999) 1422
18. Dichtel W.R., Hecht S., and Frechet J.M.J. Org. Lett. 7 (2005) 4451
19. Hahn U., Gorka M., Vogtle F., Vicinelli V., Ceroni P., Maestri M., and Balzani V. Angew. Chem., Int. Ed. 41 (2002) 3595
20. Kwon T.-H., Kim M.K., Kwon J., Shin D.-Y., Park S., Lee C.-L., Kim J.-J., and Hong J.-I. Chem. Mater. 19 (2007) 3673
21. Stewart G.M., and Fox M.A. J. Am. Chem. Soc. 118 (1996) 4354
22. Vijayalakshmi N., and Maitra U. Macromolecules 39 (2006) 7931
23. Adronov A., Gilat S.L., Frechet J.M.J., Ohta K., Neuwahl F.V.R., and Fleming G.R. J. Am. Chem. Soc. 122 (2000) 1175
24. Goodson III T. Annu. Rev. Phys. Chem. 56 (2005) 581
25. Poliakov E.Y., Chernyak V., Tretiak S., and Mukamel S. J. Chem. Phys. 110 (1999) 8161
26. Charnyak V., Minami T., and Mukamel S. J. Chem. Phys. 112 (2000) 7953
27. Shortreen M.R., Swallen S.F., Shi Z.Y., Tan W., Xu Z., Devadoss C., Moore J.S., and Kopelman R. J. Phys. Chem. B 101 (1997) 6318
28. De Schryver F.C., Vosch T., Cotlet M., Auweraer M.V.D., Mullen K., and Hofkens J. Acc. Chem. Res. 38 (2005) 514
29. Maus M., De R., Lor M., Weil T., Mitra S., Wiesler U.M., Herrman A., Hofkens J., Vosch T., Mullen K., and Schryver G.C.D. J. Am. Chem. Soc. 123 (2001) 7668
30. Ahn T.S., Thompson A.L., Bharathi P., Muller A., and Bardeen C.J. J. Phys. Chem. B 110 (2006) 19810
31. Ranasinghe M.I., Hager M.W., Gorman C.B., and Goodson III T. J. Phys. Chem. B 108 (2004) 8543
32. Ranasinghe M.I., Varnavski O.P., Pawlas J., Hauck S.I., Louie J., Hartwig J.G., and Goodson III T. J. Am. Chem. Soc. 124 (2002) 6520
33. Varnavski O., Leanov A., Liu L., Takacs J., and Goodson III T. Phys. Rev. B 61 (2000) 12732
34. Wang Y., Ranasinghe M.I., and Goodson III T. J. Am. Chem. Soc. 125 (2003) 9562
35. Samuel I.D.W., Crystall B., Rumbles G.P.L., Holmes A.B., and Friend R.H. Chem. Phys. Lett. 213 (1993) 472
36. Ley K.D., Whittle C.E., Bartberger M.D., and Schanze K.S. J. Am. Chem. Soc. 119 (1997) 3423
37. Mueller J.G., Atas E., Tan C., Schanze K.S., and Kleiman V.D. J. Am. Chem. Soc. 128 (2006) 4007
38. Guillet J. Polymer Photophysics and Photochemistry: An Introduction to the Study of Photoprocesses in Macromolecules (1987), Cambridge University Press, Cambridge, UK
39. Yang J.S., and Swager T.M. J. Am. Chem. Soc. 120 (1998) 5321
40. Peng Z., Pan Y., Xu B., and Zhang J. J. Am. Chem. Soc. 122 (2000) 6619
41. Melinger J.S., Pan Y., Kleiman V.D., Peng Z., Davis B.L., McMorrow D., and Lu M. J. Am. Chem. Soc. 124 (2002) 12002
42. Pan Y., Peng Z., and Melinger J.S. Tetrahedron 59 (2003) 5495
43. Peng Z., Melinger J.S., and Kleiman V. Photosynth. Res. 87 (2006) 115
44. Xia C.J., Fan X.W., Locklin J., and Advincula R.C. Org. Lett. 4 (2002) 2067
45. Xu M.H., Lin J., Hu Q.S., and Pu L. J. Am. Chem. Soc. 124 (2002) 14239
46. Wang J., Luo J., Liu L., Zhou Q., Ma Y., and Pei J. Org. Lett. 8 (2006) 2281
47. Nierengarten J. Pure Appl. Chem. 78 (2006) 847
48. Cotlet M., Vosch T., Habuchi S., Weil T., Muellen K., Hofkens J., and De Schryver F. J. Am. Chem. Soc. 127 (2005) 9760
49. Koese M.E., Mitchell W.J., Kopidakis N., Chang C.H., Shaheen S.E., Kim K., and Rumbles G. J. Am. Chem. Soc. 129 (2007) 14257
50. Rose A., Lugmair C.G., and Swager T.M. J. Am. Chem. Soc. 123 (2001) 11298
51. Chandrasekhar S. Liq. Cryst. 14 (1993) 3
52. Cross S.J., Goodby J.W., Hall A.W., Hird M., Kelly S.M., Toyne K.J., and Wu C. Liq. Cryst. 25 (1998) 1
53. Boden N., Bushby R.J., and Cammidge A.N. J. Am. Chem. Soc. 117 (1995) 924
54. Adam D., Schuhmacher P., Simmerer J., Haussling L., Siemensmeyer K., Etzbach K.H., Rinsdorf H., and Haarer D. Nature 371 (1994) 141
55. Zimmermann S., Wendorff J.H., and Weder C. Chem. Mater. 14 (2002) 2218
56. Schmidt-Mende L., Fechtenkotter A., Mullen K., Moons E., Friend R.H., and Mackenzie J.D. Science 293 (2001) 1119
57. Boden N., Bushby R.J., Cooke G., Lozman O.R., and Lu Z. J. Am. Chem. Soc. 123 (2001) 7915
58. Bayer A., Kopitzke J., Noll F., Seifert A., and Wendorff J.H. Macromolecules 34 (2001) 3600
59. Schönherr H., Manickam M., and Kumar S. Langmuir 18 (2002) 7082
60. McKenna M.D., Barberá J., Marcos M., and Serrano J.L. J. Am. Chem. Soc. 127 (2005) 619
61. While this manuscript is under revision, a triphenylene-based dendrimer is reported:. Qin T., Zhou G., Scheiber H., Bauer R.E., Baumgarten M., Anson C.E., List E.J.W., and Müllen K. Angew. Chem., Int. Ed. 47 (2008) 8292
62. Kang J., Wang D., Bagui M., Chakraborty S., and Peng Z. Lett. Org. Chem. 3 (2006) 674
63. Zhao Y., and Moore J.S. In: Hecht S., and Huc I. (Eds). Foldamers: Structure, Properties, and Applications (2007), Wiley-VCH, Weinheim p 75
64. Lahiri S., Thompson J.L., and Moore J.S. J. Am. Chem. Soc. 122 (2000) 11315
65. Birks J.B. Photophysics of Aromatic Molecules (1970), Wiley-Interscience, London
66. Baunsgaard D., Larsen M., Harrit N., Frederiksen J., Wilbrandt R., and Stapelfeldt H. J. Chem. Soc., Faraday Trans. 93 (1997) 1893
67. Markovitski D., Germain A., Millie P., Lecuyer P., Gallos L.K., Argyrakis P., Bens H., and Rinsdorf H. J. Phys. Chem. 99 (1995) 1005