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Copper 1,14:7,8-Diethenotetrapyrido-[2,1,6-de:2',1',6'-gh:2'',1'',6'''-na][1,3,5,8,10,12]hexaazacyclotetradecine Trifluoroacetate

Department of Chemistry, Tamkang University, Taipei 25137, Taiwan
Author to whom correspondence should be addressed.
Molecules 2000, 5(1), M133;
Submission received: 29 December 1999 / Accepted: 17 January 2000 / Published: 24 January 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m133 i001
1,14:7,8-Diethenotetrapyrido-[2,1,6-de:2,1,6-gh:2,1,6-na][1,3,5,8,10,12] hexaazacyclotetradecine (H2HAPP) was synthesized according to Ogawas method[1]. 20 mg H2HAPP was dissolved in 0.5 mL trifluoroacetic acid, then 2mL ether was added, and the white precipitate [H4HAPP(TFA)2] was filtered off and washed with diethyl ether for several times. The mixture of this white precipitate and 50 mg copper acetate was refluxed in CH3OH:CH2Cl2 (V:V, 1:1) for 1 hour, the solvent evaporated, and the orange precipitate was washed with methanol. The product was purified by diffusing diethyl ether into a TFA solution at 4°C. Brown-yellow needle crystals of CuHAPP(TFA)2 were obtained, 23 mg. Yield: 65.7%.
NMR : no NMR signal could be observed because Cu++ ion is paramagnetic.
IR (KBr): 2716 (br), 1666 (s), 1642 (s), 1619 (m), 1597 (s), 1565 (s), 1505 (m), 1467 (s), 1421 (m), 1382 (m), 1369 (m), 1360 (m), 1291 (s), 1256 (m), 1198 (s), 1169 (s), 1151 (s), 1129 (s), 1106 (m), 866 (m), 828 (m), 800 (m), 749 (w), 717 (m), 672 (m), 642 (w), 606 (m), 576 (m), 519 (w), 486 (m).
UV-Vis ( in CH3OH:CH2Cl2, V:V, 1:1): 329.5, 281.0, 224.5 (spectra is pH sensitive).
FAB-MS ([M-1]+): 448.
Anal. Calc. for C28H14N6O4F6Cu (675.5): C 49.74, H 2.07, N 12.43 %; Found: C 49.70, H 2.32, N 12.15%.

Supplementary Materials


Support for this research provided by the National Science Council, Taiwan is gratefully acknowledged.


  1. Ogawa, S.; Yamaguchi, T.; Gotoh, N. J. Chem. Soc., Perkin Trans. I 1974, 976.
Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Wang, W.-J.; Liu, H.-Y.; Chuang, K.-S.; Luo, C.-F. Copper 1,14:7,8-Diethenotetrapyrido-[2,1,6-de:2',1',6'-gh:2'',1'',6'''-na][1,3,5,8,10,12]hexaazacyclotetradecine Trifluoroacetate. Molecules 2000, 5, M133.

AMA Style

Wang W-J, Liu H-Y, Chuang K-S, Luo C-F. Copper 1,14:7,8-Diethenotetrapyrido-[2,1,6-de:2',1',6'-gh:2'',1'',6'''-na][1,3,5,8,10,12]hexaazacyclotetradecine Trifluoroacetate. Molecules. 2000; 5(1):M133.

Chicago/Turabian Style

Wang, Wen-Jwu, Hai-Yang Liu, Kuo-Shen Chuang, and Chi-Fong Luo. 2000. "Copper 1,14:7,8-Diethenotetrapyrido-[2,1,6-de:2',1',6'-gh:2'',1'',6'''-na][1,3,5,8,10,12]hexaazacyclotetradecine Trifluoroacetate" Molecules 5, no. 1: M133.

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