Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2023; 55(16): 2595-2601
DOI: 10.1055/a-2079-3865
DOI: 10.1055/a-2079-3865
paper
Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry
Self-Complementary Dimer of Zinc(II) Porphyrins through Coordination with Oxygen Ligands
We acknowledge financial support from the National Natural Science Foundation of China (21971211 and 22171232), the Natural Science Foundation of Zhejiang Province (2022XHSJJ007), the Qiantang River Talent Foundation (QJD1902029), Westlake University, and Zhejiang Normal University.
Dedicated to Professor Guoqiang Lin on the occasion of his 80th birthday for his great contributions to the development of organic chemistry.
Abstract
Oxygen ligands have been shown to play a critical role in the formation and organization of metalloporphyrin assemblies and natural chlorosomes. In this work, mutually complementary head-to-tail dimers of zinc(II) porphyrins were synthesized through the coordination of zinc with the imide group and 7-oxanorbornene oxygen ligands. UV/Vis absorption and emission, 1H NMR as well as FT-IR analyses were used to determine the structure. The dimerization association constant K has been determined to be 5.6 M–1 and 29 M–1, respectively, by the dilution experiment.
Key words
metalloporphyrins - self-assemble - aggregation - coordination - oxygen ligands - dimerizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2079-3865.
- Supporting Information
Publication History
Received: 23 February 2023
Accepted after revision: 24 April 2023
Accepted Manuscript online:
24 April 2023
Article published online:
22 May 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Beletskaya I, Tyurin VS, Tsivadze AY, Guilard R, Stern C. Chem. Rev. 2009; 109: 1659
- 2 Choi M.-S, Yamazaki T, Yamazaki I, Aida T. Angew. Chem. Int. Ed. 2004; 43: 150
- 3 Ogawa K, Kobuke Y. J. Photochem. Photobiol., C 2006; 7: 1
- 4 Non-Covalent Multi-Porphyrin Assemblies: Synthesis and Properties. Alessio E. Springer; Heidelberg: 2006
- 5 Imamura T, Fukushima K. Coord. Chem. Rev. 2000; 198: 133
- 6 Maeda C, Kamada T, Aratani N, Osuka A. Coord. Chem. Rev. 2007; 251: 2743
- 7 Balaban TS. Acc. Chem. Res. 2005; 38: 612
- 8 Elemans JA. A. W, van Hameren R, Nolte RJ. M, Rowan AE. Adv. Mater. 2006; 18: 1251
- 9 Haycock RA, Yartsev A, Michelsen U, Sundström V, Hunter CA. Angew. Chem. Int. Ed. 2000; 39: 3616
- 10 Hunter CA, Sarson LD. Angew. Chem. Int. Ed. Engl. 1994; 33: 2313
- 11 Huber V, Katterle M, Lysetska M, Würthner F. Angew. Chem. Int. Ed. 2005; 44: 3147
- 12 Li Y, Li X, Li Y, Liu H, Wang S, Gan H, Li J, Wang N, He X, Zhu D. Angew. Chem. Int. Ed. 2006; 45: 3639
- 13 Haino T, Fujii T, Fukazawa Y. Tetrahedron Lett. 2005; 46: 257
- 14 Haino T, Fujii T, Fukazawa Y. J. Org. Chem. 2006; 71: 2572
- 15 van Hameren R, Schon P, van Buul AM, Hoogboom J, Lazarenko SV, Gerritsen JW, Engelkamp H, Christianen PC. M, Heus HA, Maan JC, Rasing T, Speller S, Rowan AE, Elemans JA. A. W, Nolte RJ. M. Science 2006; 314: 1433
- 16 van Hameren R, van Buul AM, Castriciano MA, Villari V, Micali N, Schon P, Speller S, Scolaro LM, Rowan AE, Elemans JA. A. W, Nolte RJ. M. Nano Lett. 2008; 8: 253
- 17 Zhang Y, Chen P, Liu M. Chem. Eur. J. 2008; 14: 1793
- 18 Xiao Z.-Y, Zhao X, Jiang X.-K, Li Z.-T. Org. Biomol. Chem. 2009; 7: 2540
- 19 Yoshiaki K. Eur. J. Inorg. Chem. 2006; 2333
- 20 For a recent review, see: Xue Z.-X, Li W.-S. In Ladder Polymers: Synthesis, Properties, Applications and Perspectives, Chap. 5. Xia Y, Yamaguchi M, Luh T.-Y. Wiley-VCH; Weinheim: 2023
- 21 Maeda C, Yamaguchi S, Ikeda C, Shinokubo H, Osuka A. Org. Lett. 2008; 10: 549
- 22 Camara-Campos A, Hunter CA, Tomas S. Proc. Natl. Acad. Sci. U. S. A. 2006; 103: 3034
- 23 Vinodu M, Stein Z, Goldberg I. Inorg. Chem. 2004; 43: 7582
- 24 Tsuda A, Sakamoto S, Yamaguchi K, Aida T. J. Am. Chem. Soc. 2003; 125: 15722
- 25 Chi X, Guerin AJ, Haycock RA, Hunter CA, Sarson LD. J. Chem. Soc., Chem. Commun. 1995; 2563
- 26 Stibrany RT, Vasudevan J, Knapp S, Potenza JA, Emge T, Schugar HJ. J. Am. Chem. Soc. 1996; 118: 3980
- 27 Shao X.-B, Jiang X.-K, Zhu S.-Z, Li Z.-T. Tetrahedron 2004; 60: 9155
- 28 Michelsen U, Hunter CA. Angew. Chem. Int. Ed. 2000; 39: 764
- 29 Kamada T, Aratani N, Ikeda T, Shibata N, Higuchi Y, Wakamiya A, Yamaguchi S, Kim KS, Yoon ZS, Kim D, Osuka A. J. Am. Chem. Soc. 2006; 128: 7670
- 30 Imamura T, Funatsu K, Ye S, Morioka Y, Uosaki K, Sasaki Y. J. Am. Chem. Soc. 2000; 122: 9032
- 31 Lee SJ, Mulfort KL, Zuo X, Goshe AJ, Wesson PJ, Nguyen ST, Hupp JT, Tiede DM. J. Am. Chem. Soc. 2008; 130: 836
- 32 Muraoka T, Kinbara K, Aida T. Nature 2006; 440: 512
- 33 Nakamura Y, Aratani N, Osuka A. Chem. Asian J. 2007; 2: 860
- 34 Kai H, Nara S, Kinbara K, Aida T. J. Am. Chem. Soc. 2008; 130: 6725
- 35 Haycock RA, Hunter CA, James DA, Michelsen U, Sutton LR. Org. Lett. 2000; 2: 2435
- 36 Koepf M, Wytko JA, Bucher J.-P, Weiss J. J. Am. Chem. Soc. 2008; 130: 9994
- 37 Raymond JE, Bhaskar A, Goodson T, Makiuchi N, Ogawa K, Kobuke Y. J. Am. Chem. Soc. 2008; 130: 17212
- 38 D’Souza F, Smith PM, Rogers L, Zandler ME, Shafiqul Islam DM, Araki Y, Ito O. Inorg. Chem. 2006; 45: 5057
- 39 Balaban TS, Goddard R, Linke-Schaetzel M, Lehn J.-M. J. Am. Chem. Soc. 2003; 125: 4233
- 40 Knapp S, Vasudevan J, Emge TJ, Arison BH, Potenza JA, Schugar HJ. Angew. Chem. Int. Ed. 1998; 37: 2368
- 41 Liu H.-y, Huang J.-w, Tian X, Jiao X.-d, Luo G.-t, Ji L.-n. Chem. Commun. 1997; 1575
- 42 Bonar-Law RP, Mackay LG, Sanders JK. M. J. Chem. Soc., Chem. Commun. 1993; 456
- 43 Kobuke Y, Miyaji H. J. Am. Chem. Soc. 1994; 116: 4111
- 44 Gao Y, Zhang X, Ma C, Li X, Jiang J. J. Am. Chem. Soc. 2008; 130: 17044
- 45 Senge MO, Speck M, Wiehe A, Dieks H, Aguirre S, Kurreck H. Photochem. Photobiol. 1999; 70: 206
- 46 Balaban TS, Eichhöfer A, Lehn J.-M. Eur. J. Org. Chem. 2000; 4047
- 47 Jochum T, Reddy CM, Eichhöfer A, Buth G, Szmytkowski J, Kalt H, Moss D, Balaban TS. Proc. Natl. Acad. Sci. U. S. A. 2008; 105: 12736
- 48 Mizutani T, Kurahashi T, Murakami T, Matsumi N, Ogoshi H. J. Am. Chem. Soc. 1997; 119: 8991
- 49 Huijser A, Suijkerbuijk BM. J. M, Klein Gebbink RJ. M, Savenije TJ, Siebbeles LD. A. J. Am. Chem. Soc. 2008; 130: 2485
- 50 Huang X, Zhao F, Li Z, Tang Y, Zhang F, Tung C.-H. Langmuir 2007; 23: 5167
- 51 Huang X, Zhao F, Li Z, Huang L, Tang Y, Zhang F, Tung C.-H. Chem. Lett. 2007; 36: 108
- 52 Alessio E, Macchi M, Heath SL, Marzilli LG. Inorg. Chem. 1997; 36: 5614
- 53 Matano Y, Matsumoto K, Terasaka Y, Hotta H, Araki Y, Ito O, Shiro M, Sasamori T, Tokitoh N, Imahori H. Chem. Eur. J. 2007; 13: 891
- 54 Atefi F, McMurtrie JC, Arnold DP. Dalton Trans. 2007; 2163
- 55 Atefi F, McMurtrie JC, Turner P, Duriska M, Arnold DP. Inorg. Chem. 2006; 45: 6479
- 56 Wang H.-W, Liu Z.-C, Chen C.-H, Lim T.-S, Fann W, Chao C.-G, Yu J.-Y, Lee S.-L, Chen C.-h, Huang S.-L, Luh T.-Y. Chem. Eur. J. 2009; 15: 5719
- 57 Jordan P, Fromme P, Witt HT, Klukas O, Saenger W, Krausz N. Nature 2001; 411: 909
- 58 Lin W.-Y, Wang H.-W, Liu Z.-C, Xu J, Chen C.-W, Yang Y.-C, Huang S.-L, Yang H.-C, Luh T.-Y. Chem. Asian J. 2007; 2: 764
- 59 Hou J.-L, Yi H.-P, Shao X.-B, Li C, Wu Z.-Q, Jiang X.-K, Wu L.-Z, Tung C.-H, Li Z.-T. Angew. Chem. Int. Ed. 2006; 45: 796
- 60 Lakowicz JR. Principles of Fluorescence Spectroscopy, 3rd ed. Springer; New York: 2006
- 61 Connors KA. Binding Constants, The Measurement of Molecular Complex Stability. Wiley-Interscience; New York: 1987