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Synlett 2015; 26(11): 1620-1624
DOI: 10.1055/s-0034-1378710
DOI: 10.1055/s-0034-1378710
letter
A Fourfold Benzodehydroannuleno-Fused Porphyrazine
Weitere Informationen
Publikationsverlauf
Received: 20. März 2015
Accepted after revision: 11. Mai 2015
Publikationsdatum:
11. Juni 2015 (online)
![](https://www.thieme-connect.de/media/synlett/201511/lookinside/thumbnails/st-2015-b0201-l_10-1055_s-0034-1378710-1.jpg)
Dedicated to Professor K. Peter C. Vollhardt – eminent chemist and inspirational character
Abstract
Four benzodehydroannulene subunits were implemented on a dibenzoquinoxalinopoprhyrazine core using efficient palladium-mediated alkyne coupling and oxidative acetylene coupling on phenanthrene dione precursors. Despite the significant amount of strain in system, as evidenced by X-ray analysis of an immediate precursor, porphyrazine assembly leads to an extended model for N-doped graphyne with photosensitizing properties.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378710.
- Supporting Information
-
References
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- 14 Compound 6 A solution of 5 (500 mg, 0.39 mmol) and Cu(OAc)2 in pyridine (10 mL) was stirred for 2 h at 60 °C. After cooling to r.t. CHCl3 (50 mL) was added, and the mixture was washed successively with 1 N HCl (50 mL), H2O (2 × 50 mL), and sat. aq NaCl (50 mL). The organic layer was separated, dried over Na2SO4, filtered, and excess solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel with CHCl3 to yield a bright yellow solid (450 mg, 0.35 mmol, 90%). 1H NMR (400 MHz, CDCl3): δ = 8.51 (s, 2 H, CHphenan), 7.74 (s, 2 H,, CHphenan), 7.35 (d, 3 J HH = 8.2 Hz, 12 H, CHarom), 7.10 (d, 3 J HH = 8.2 Hz, 12 H, CHarom), 7.08 (s, 2 H, CHarom), 6.42 (s, 2 H, CHarom), 4.19 (br s, 4 H, OCH2), 3.91 (s, 6 H, OCH3), 3.69 (br s, 4 H, OCH2), 3.39(s, 6 H, OCH3), 2.32 (s, 18 H, CH3) ppm. 13C NMR (126 MHz, CDCl3): δ = 149.69, 149.32, 142.56, 136.28, 132.79, 130.93, 130.24, 129.06, 128.99, 128.72, 128.24, 124.42, 118.43, 118.30, 116.33, 113.54, 101.14, 93.10, 92.46, 92.42, 83.76, 82.46, 56.03, 55.72, 55.46, 20.95 ppm. MALDI-MS (DCTB, positive ion mode): m/z = 1279.55 [M + H]+.
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