This study presents the first synthesis and characterization of a new high energy compound [1,2,3,4]tetrazino[5,6-e][1,2,3,4]tetrazine 1,3,6,8-tetraoxide (TTTO). It was synthesized in ten steps from 2,2-bis(tert-butyl-NNO-azoxy)acetonitrile. The synthetic strategy was based on the sequential closure of two 1,2,3,4-tetrazine 1,3-dioxide rings by the generation of oxodiazonium ions and their intramolecular coupling with tert-butyl-NNO-azoxy groups. The TTTO structure was confirmed by single-crystal X-ray.

The search of the new low-melting high energetic materials, which match the performance of TNAZ and more available, is the barest necessity. The syntheses of several novel zero-hydrogen but nitrogen and oxygen rich high energetic heterocycles, such as bridged nitrofurazans, were undertaken to test the hypothesis that accumulate furazan ring in such molecule could effectively serve in construction of energetically interesting materials. Eight dinitro trifurazans were synthesized and tested. The series of compounds was prepared in three±®ve stages from the 3,4-diaminofurazan (10). Oxy bridge was formed by utilizing hydroxyfurazans as nucleophiles. Azo bridge was prepared by oxidizing coupling of amino groups with KMnO 4 in acid medium. Transformation of azo bridge to azoxy one was accomplished by mixture of (NH 4 ) 2 S 2 O 8 and oleum. The set of trifurazans represents a new class of low-melting high energetic materials which are among the most potent C x H y N z O wexplosives known. The isomeric diazoxyfurazans, (28), (29), and (30), differ dramatically in their properties. Liquid diazoxy compound (28) has density of 1.8 g/cm 3 and is reach a record ®gure for C x H y N z O w -oil known.

A derivative of dipyridylethylene 2 was synthesized in order to study intermolecular coordination between the 18-crown-6 ether units of bis-crown stilbene 1 and the NH3 + groups of 2. In acetonitrile solution, the formation of a supramolecular complex is evidenced by a considerable upfield shift of the 1H NMR signals from the aromatic and olefinic protons. Emission quenching and the appearance of a new absorption band in the visible spectral region indicate the formation of a charge-transfer complex. The addition of Ba2+ to a solution of the complex leads to significant fluorescence enhancement and to the disappearance of the charge-transfer absorption band.

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