Synthesis, Optical, and Antioxidant Studies of Anthraquinone-core-based Dendrimers with N-Phenylcarbazole as Surface Group
Perumal Rajakumar A D , Nagarathinam Venkatesan A , Karuppannan Sekar B , Subramani Nagaraj C and Ramasamy Rengasamy C
+ Author Affiliations
- Author Affiliations
A Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India.
B Department of Chemistry, Anna University–University College of Engineering, Dindigul 624 622, India.
C Centre for Advanced Studies in Botany, University of Madras, Guindy Campus, Chennai 600 025, India.
D Corresponding author. Email: perumalrajakumar@gmail.com
Australian Journal of Chemistry 67(4) 636-643 https://doi.org/10.1071/CH13521
Submitted: 28 September 2013 Accepted: 22 November 2013 Published: 6 January 2014
Abstract
Synthesis of hyperbranched dendrimers up to third generation with N-phenylcarbazole as surface group and anthraquinone as the core unit has been achieved. The fluorescence decay studies of the dendrimers indicate that generation growth alters the relaxation time. The highly branched third-generation dendrimer has a longer relaxation time than the zero-, first-, and second-generation dendrimers. Similarly, higher-generation dendrimers show better antioxidant behaviour with 1,1-diphenyl-2-picryl hydrazyl than the lower-generation dendrimers.
References
[1] (a) J. F. Ambrose, R. F. Nelson, J. Electrochem. Soc. 1968, 115, 1159.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXltFarsbo%3D&md5=4f4cfef2a2eddd07175a132b203594e1CAS |
(b) F. Ambrose, L. L. Carpenter, R. F. J. Nelson, Electrochem. Soc. 1975, 122, 876.
| Crossref | GoogleScholarGoogle Scholar |
[2] (a) P. Furuta, J. Brooks, M. E. Thompaon, J. M. J. J. Fréchet, Am. Chem. Soc 2003, 125, 13165.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosVCksbc%3D&md5=7d0857aada5c3ece740ab91543104a11CAS |
(b) T. W. Kwon, M. M. Alam, S. A. Jenekhe, Chem. Mater. 2004, 16, 4657.
| Crossref | GoogleScholarGoogle Scholar |
(c) S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819.
| Crossref | GoogleScholarGoogle Scholar |
[3] (a) M. Sangermano, G. Malucelli, A. Priola, S. Lengvinaite, J. Simokaitiene, J. V. Grazulevicius, Eur. Polym. J. 2005, 41, 475.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXnsVGmsg%3D%3D&md5=5461ccf061414edd85b96b40fe4d4fa4CAS |
(b) Z. Gomurashvili, Y. Hua, J. V. Crivello, Macromol. Chem. Phys. 2001, 202, 2133.
| Crossref | GoogleScholarGoogle Scholar |
(c) D. R. Prudhomme, Z. Wang, C. J. Rizzo, J. Org. Chem. 1997, 62, 8257.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) Y. Shirota, J. Mater. Chem. 2000, 10, 1.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXotVKgtbg%3D&md5=be860930f93b7c6354d48c9735a2eb2aCAS |
(b) J. Kido, K. Hongawa, K. Okuyama, K. Nagai, Appl. Phys. Lett. 1993, 63, 2627.
| Crossref | GoogleScholarGoogle Scholar |
[5] (a) U. Boas, P. M. H. Heegaard, Chem. Commun. 1996, 1523.
(b) L. Balogh, D. R. Swanson, D. A. Tomalia, G. L. Hagnauer, A. T. McManus, Nano Lett. 2001, 1, 18.
| Crossref | GoogleScholarGoogle Scholar |
[6] J. Recker, D. J. Tomcik, J. R. Parquette, J. Am. Chem. Soc. 2000, 122, 10298.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXmvFGiu7c%3D&md5=a9bcd4707f5bc638cceb14f20ca9d421CAS |
[7] (a) B. P. Hay, E. J. Werner, K. N. Raymond, Bioconjug. Chem. 2004, 15, 1496.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXovVGqtrk%3D&md5=1b3cc7c5500c6ec26da7420460e6417cCAS | 15546220PubMed |
(b) M. Doubrovin, I. Serganova, P. Mayer-Kuckuk, V. Ponomarev, R. G. Blasberg, Bioconjug. Chem. 2004, 15, 1376.
| Crossref | GoogleScholarGoogle Scholar |
[8] K. Kono, M. Liu, J. M. J. Fréchet, Bioconjug. Chem. 1999, 10, 1115.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXms1yiurc%3D&md5=2e55184b54a284402f83ffa60841ef0eCAS | 10563782PubMed |
[9] Y. Y. Cheng, J. R. Wang, T. L. Roa, X. X. He, T. W. Xu, Front. Biosci. 2008, 13, 1447.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhs1Cgs7s%3D&md5=0e25ae02cc7e956b75686bd69cf42d47CAS |
[10] D. Tyssen, S. A. Henderson, A. Johnson, J. Sterjovski, K. Moore, J. La, M. Zanin, S. Sonza, P. Karellas, M. P. Giannis, G. Krippner, S. Wesselingh, T. McCarthy, P. R. Gorry, P. A. Ramsland, R. Cone, J. R. A. Paull, G. R. Lewis, G. Tachedjian, PLoS ONE 2010, 5, e12309.
| Crossref | GoogleScholarGoogle Scholar | 20808791PubMed |
[11] M. Sakamoto, A. Veno, H. Mihare, Chem. Commun. 2000, 1741.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXmtl2mt7s%3D&md5=22aaa364c793f176116673afdce59167CAS |
[12] S. Ghosh, K. A. Banthia, Tetrahedron Lett. 2002, 43, 6457.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmsVSqur8%3D&md5=b84269aee1b24164efba15bc88cdedeaCAS |
[13] P. Rajakumar, K. Ganesan, Synlett 2004, 2236.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXosFyjt7o%3D&md5=1fa21e2de31ecd5ae7b92facabe2366bCAS |
[14] P. Rajakumar, K. Ganesan, S. Jayavelu, K. Murugesan, Synlett 2005, 1121.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXktlyntrg%3D&md5=3cf2e6d04fea9574de8ea124ed926600CAS |
[15] P. Rajakumar, K. Ganesan, Tetrahedron Asymmetry 2005, 16, 2295.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXmtFCrs7Y%3D&md5=9745622e895c9484425467c7891ba736CAS |
[16] P. Rajakumar, N. Venkatesan, K. Sekar, S. Nagaraj, R. Rengasamy, Eur. J. Med. Chem. 2010, 45, 1220.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhvF2qs7g%3D&md5=130796241a52ead834253755e6988c6aCAS | 20034709PubMed |
[17] J. C. Antilla, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 11684.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xms12rtb8%3D&md5=191c729298b7959c18c0958d798b3ec4CAS | 12296734PubMed |
[18] H. Fenglin, K. Ruili, H. Bao, M. Liang, Fitoterapia 2004, 75, 14.
| Crossref | GoogleScholarGoogle Scholar |
[19] Y. Li, Y. Y. Cheng, T. W. Xu, Curr. Drug Discov. Technol. 2007, 4, 246.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVKitA%3D%3D&md5=4be8c4bc257163e5edc68bcc84d85d27CAS | 18045087PubMed |
[20] Y. Rajeshwar, G. P. Senthil Kumar, M. Gupta, U. K. Mazumdar, Eur. Bull. Drug Res. 2005, 13, 31.
[21] C. Y. Lee, A. Sharma, J. E. Cheong, J. L. Nelson, Bioorg. Med. Chem. Lett. 2009, 19, 6326.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlWlsrfP&md5=a9c0c7066d173448d42d9dd9f296b93dCAS | 19822425PubMed |
