Citation: Yu-Xuan FAN, Tai-Yan YUAN, Qing-Yang LV, Min-Zhi LI, Wei-Hua ZHU, Xu LIANG. Synthesis and Electronic Structure of Triazasubporphyrin with Peripherally Low Symmetric Push-pull Substitutions[J]. Chinese Journal of Structural Chemistry, ;2020, 39(1): 36-40. doi: 10.14102/j.cnki.0254-5861.2011-2375 shu

Synthesis and Electronic Structure of Triazasubporphyrin with Peripherally Low Symmetric Push-pull Substitutions

School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China

Corresponding author: Wei-Hua ZHU, sayman@ujs.edu.cn Xu LIANG, liangxu@ujs.edu.cn
Received Date: 21 March 2019
Accepted Date: 21 June 2019

Fund Project: the National Natural Science Foundation of China 21701058the Natural Science Foundation of Jiangsu province BK20160499the State Key Laboratory of Coordination Chemistry SKLCC1817the Key Laboratory of Functional Inorganic Material Chemistry (Heilongjiang University) of Ministry of Education, the China post-doc foundation 2018M642183the Lanzhou Entrepreneurial and Innovative Talents Project 2018-RC-105the Jiangsu University 17JDG035

Figures(3)

Peripherally low symmetric substitution with electron-donating (EDG) and electron-withdrawing (EWG) substituents caused the rational modulation of geometric structure and even the electronic structure of triazasubporphyrin, the smallest 14π conjugated aza-porphyrinoids. Both structural characterization and spectroscopic investigation were discussed to provide an in-depth understanding of the relationship between peripheral push-pull substituents and SubPz core.
- triazasubporphyrin,
- push-pull effect,
- electronic structure,
- seterochemistry
1. [1]
  Claessens, C. G.; González-Rodríguez, D.; Rodríguez-Morgade, M. S.; Medina, A.; Torres, T. Subphthalocyanines, subporphyrazines, and subporphyrins: singular nonplanar aromatic systems. Chem. Rev. 2014, 114, 2192−2277. doi: 10.1021/cr400088w
2. [2]
  Claessens, C. G.; González-Rodríguez, D.; Torres, T. Subphthalocyanines: singular nonplanar aromatic compounds. Chem. Rev. 2002, 102, 835−854. doi: 10.1021/cr0101454
3. [3]
  Rauschnabel, J.; Hanack, M. New derivatives and homologues of subphthalocyanine. Tetra. Lett. 1995, 36, 1629−1632. doi: 10.1016/0040-4039(95)00124-U
4. [4]
  Rodríguez-Morgade, M. S.; Esperanza, S.; Torres, T.; Barbera J. Synthesis, characterization, and properties of subporphyrazines: a new class of nonplanar, aromatic macrocycles with absorption in the green region. Chem. Eur. J. 2005, 11, 354−360. doi: 10.1002/chem.200400787
5. [5]
  Kobayashi, N.; Ishizaki, T.; Ishii, K.; Konami, H. Synthesis, spectroscopy, and molecular orbital calculations of subazaporphyrins, subphthalocyanines, subnaphthalocyanines, and compounds derived Therefrom by ring expansion. J. Am. Chem. Soc. 1999, 121, 9096−9110. doi: 10.1021/ja983325c
6. [6]
  Stork, J. R.; Brewer, J. J.; Fukuda, T.; Fitzgerald, J. P.; Yee, G. T.; Nazarenko, A. Y.; Kobayashi N.; Durfee, W. S. Chloro and hydroxo forms of a boron(III) subtriazaporphyrin macrocycle. Inorg. Chem. 2006, 45, 6148−6151. doi: 10.1021/ic051093u
7. [7]
  Liang, X.; Shimizu, S.; Kobayashi, N. Sizeable red-shift of absorption and fluorescence of subporphyrazine induced by peripheral push and pull substitution. Chem. Commun. 2014, 50, 13781−13784. doi: 10.1039/C4CC05943C
8. [8]
  Higashino, T.; Rodríguez-Morgade, M. S.; Osuka, A.; Torres, T. Peripheral arylation of subporphyrazines. Chem. Eur. J. 2013, 19, 10353−10359. doi: 10.1002/chem.201301140
9. [9]
  Shimizu, S.; Otaki, T.; Yamazaki, Y.; Kobayashi, N. Synthesis and properties of β, β-sp³-hybridized subphthalocyanine analogues. Chem. Commun. 2012, 48, 4100−4102. doi: 10.1039/c2cc30511a
10. [10]
  Mack, J.; Bunya, M.; Shimizu, Y.; Uoyama, H.; Komobuchi, N.; Okujima, T.; Uno, H.; Ito, S.; Stillman, M. J.; Ono, N.; Kobayashi, N. Application of MCD spectroscopy and TD-DFT to nonplanar core-modified tetraennoporphyrins: effect of reduced symmetry on nonplanar porphyrinoids. Chem. Eur. J. 2008, 14, 5001−5020. doi: 10.1002/chem.200701611
11. [11]
  Mack, J.; Asano, Y.; Kobayashi, N.; Stillman, M. J. Application of MCD spectroscopy and TD-DFT to a highly non-planar porphyrinoid ring system. New insights on red-shifted porphyrinoid spectral bands. J. Am. Chem. Soc. 2005, 127, 17697−17711. doi: 10.1021/ja0540728
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