M133

Molecules 2000, 5, M133

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

Wen-Jwu Wang*, Hai-Yang Liu, Kuo-Shen Chuang and Chi-Fong Luo

Department of Chemistry, Tamkang University, Taipei 25137, Taiwan. Tel. +886-02-26215656-2530 (E-mail: [email protected])

Received: 29 December 1999 / Accepted: 17 January 2000 / Published: 24 January 2000

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 %.

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

Reference

1. Ogawa, S.; Yamaguchi, T.; Gotoh, N. J. Chem. Soc., Perkin Trans. I 1974, 976.

Sample Availability: Available from the authors and from MDPI.