Solid-state structure and optical properties of highly fluorescent diketopyrrolopyrrole derivatives synthesized by cross-coupling reaction

Tetrahedron

Volumn 66, Issue 21, 2010, Pages 3736-3741

  Kuwabara, Junpei ^a   Yamagata, Takuya ^a   Kanbara, Takaki ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Cross coupling reaction; Diketopyrrolopyrrole; Fluorescence; Solid state structure

Indexed keywords

DIKETOPYRROLOPYRROLE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON; PRIORITY JOURNAL; QUANTUM YIELD; SOLID STATE; SOLUTION AND SOLUBILITY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 77951104180     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.067     Document Type: Article

References (38)

1. Wallquist O., and Lenz R. Macromol. Symp. 187 (2002) 617-629
2. Hao Z., and Iqbal A. Chem. Soc. Rev. 26 (1997) 203-213
3. Zambounis J.S., Hao Z., and Iqbal A. Nature 388 (1997) 131-132
4. Wallquist O. In: Smith H.M. (Ed). High Performance Pigments (2002), Wiley-VCH, Weinheim 159-184
5. Zhang K., and Tieke B. Macromolecules 41 (2008) 7287-7295
6. Fischer G.M., Ehlers A.P., Zumbusch A., and Daltrozzo E. Angew. Chem., Int. Ed. 46 (2007) 3750-3753
7. Cao D., Liu Q., Zeng W., Han S., Peng J., and Liu S. Macromolecules 39 (2006) 8347-8355
8. Fukuda M., Kodama K., Yamamoto H., and Mito K. Dyes Pigments 63 (2004) 115-125
9. Qu S., Wu W., Hua J., Kong C., Long Y., and Tian H. J. Phys. Chem. C 114 (2010) 1343-1349
10. Zhou E., Wei Q., Yamakawa S., Zhang Y., Tajima K., Yang C., and Hashimoto K. Macromolecules 43 (2010) 821-826
11. Bijleveld J.C., Zoombelt A.P., Mathijssen S.G.J., Wienk M.M., Turbiez M., de Leeuw D.M., and Janssen R.A.J. J. Am. Chem. Soc. 131 (2009) 16616-16617
12. Huo L., Hou J., Chen H., Zhang S., Jiang Y., Chen T.L., and Yang Y. Macromolecules 42 (2009) 6564-6571
13. Zou Y., Gendron D., Badrou-Aïch R., Najari A., Tao Y., and Leclerc M. Macromolecules 42 (2009) 2891-2894
14. Yu C., Chen C., Chan S., Hwang G., and Ting C. Chem. Mater. 21 (2009) 3262-3269
15. Tamayo A.B., Walker B., and Nguyen T. J. Phys. Chem. C 112 (2008) 11545-11551
16. Wienk M.M., Turbiez M., Gilot J., and Janssen R.A.J. Adv. Mater. 20 (2008) 2556-2560
17. Bürgi L., Turbiez M., Pfeiffer R., Bienewald F., Kirner H., and Winnewisser C. Adv. Mater. 20 (2008) 2217-2224
18. Tantiwiwat M., Tamayo A., Luu N., Dang X., and Nguyen T. J. Phys. Chem. C 112 (2008) 17402-17407
19. Recent examples of a postfunctionalization of DPP.
20. Luňák Jr. S., Vyňuchal J., Vala M., Havel L., and Hrdina R. Dyes Pigments 82 (2009) 102-108
21. Guo E.Q., Ren P.H., Zhang Y.L., Zhang H.C., and Yang W.J. Chem. Commun. (2009) 5859-5861
22. Recent examples of fluorophore syntheses by organometallic catalysts.
23. Bhosale S.V., Kalyankar M.B., Bhosake S.V., Langford S.J., Reid E.F., and Hogan C.F. New J. Chem. 33 (2009) 2409-2413
24. Shimizu M., Tatsumi H., Mochida K., Shimono K., and Hiyama T. Chem. Asian J. 4 (2009) 1289-1297
25. Son H., Han W., Yoo D., Min K., Kwon S., Ko J., and Kang S.O. J. Org. Chem. 74 (2009) 3175-3178
26. Ulrich G., Ziessel R., and Harriman A. Angew. Chem., Int. Ed. 47 (2008) 1184-1201
27. Yamagata T., Kuwabara J., and Kanbara T. Tetrahedron Lett. 51 (2010) 1596-1599
28. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176-4211
29. Bedford R.B., Cazin C.S.J., and Holder D. Coord. Chem. Rev. 248 (2004) 2283-2321
30. Langhals H., Potrawa T., Nöth H., and Linti G.A. Angew. Chem., Int. Ed. Engl. 28 (1989) 478-480
31. Biscoe M.R., Barder T.E., and Buchwald S.L. Angew. Chem., Int. Ed. 46 (2007) 7232-7235
32. 2(all reflections)=0.1038, GOF=1.052. CCDC 765334.
33. 2(all reflections)=0.2679, GOF=1.078. CCDC 765335.
34. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision D.01 (2004), Gaussian, Wallingford CT
35. Foster J.P., and Weinhold F. J. Am. Chem. Soc. 102 (1980) 7211-7218
36. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Version 3.1.
37. Dennington II R., Keith T., and Millam J. GaussView, Version 4.1 (2007), Semichem, Shawnee Mission, KS
38. Katoh R., Suzuki K., Furube A., Kotani M., and Tokumaru K. J. Phys. Chem. C 113 (2009) 2961-2965