2.4.5.7- Tetranitro-9-fluorenone

Polynitro derivatives of monocychc aromatic systems (trinitrobenzene, trinitrotoluene, tetranitro-iV-methylaniline, trinitrophenol, etc.) have long been used as explosives [1]. It has been found that a series of polynitroderivatives of biphenyl, diphenylmethane and 1,2-diphenylethylene (stilbene) are explosives liable to detonate on grinding or impact [2]. The same may be true of other polynitro derivatives of polycyclic systems not normally used as explosives (e.g. polynitro-fluorenones, -carbazoles, etc. Penta- and hexa-nitrobenzophenones are also high-energy explosives [3]. The thermal stability of 33 polynitroaromatics was studied by DTA [4]. Two empirical equations relating the heat of decomposition to the heat of detonation have been developed and used to calculate the heats of detonation for 47 polynitroaryl compoimds [5]. 

Figure 2.67a R = R = Me) displays solvoluminescence. These compounds also react with acceptor molecules or metal ions M+ (M+ = Ag+, Tl+). Structures of [Au3(MeOC NMe)3] with the acceptors 2,4,7-trinitro-9-fluorenone and 2,3,4,7-tetranitro-9-fluor-enone consist of columns of planar molecules showing the pattern... 

Finally, secondary Au- -C bonds have been found in some adducts of the triangular gold(I) complex [Au3(MeN=COMe)3], where they function as electron donors, with nitro-9-fluorenones as acceptors. The solid-state structures of [Au3(MeN=COMe)3]-[2,4,7-trinitro-9-fluorenone] and [Au3(MeN=COMe)3]-[2,4,5,7-tetranitro-9-fluorenone] [50] consist of one-dimensional arrays in which the planar gold(I) trimers and the nearly planar organic molecules are interleaved with the gold trimers, making face-to-face contact with the nitro-aromatic portion of... 

Figure 5.27 1-D polymer of (a) [Au3(MeN=COMe)3]-[2,4,5,7-tetranitro-9-fluorenone] (b) [Au3(MeN=COMe)3]-[2,4,7-trinitro-9-fluorenone] showing the Au- -C interactions.

Another interesting characteristic of the trinuclear [Au3(CH3N = COR)3] (R = Me, Et) complexes is that they can act as electron donors with organic acceptor molecules such as nitro-9-fluorenones [46]. Thus, they form adducts with 2,4,7-trinitro-9-fluorenone (deep yellow and red R=Me, Et, respectively), 2,4,5,7-tetranitro-9-fluorenone (red R = Me), 2,7-dinitro-9-fluorenone (red R = Et). The solid state structures of the complexes formed with [Au3(CH3N = COMe)3] and 2,4,7-trinitro-9-fluorenone or 2,4,5,7-tetranitro-9-fluorenone consist of planar gold(I) trimers interleaved with the nitro-9-fluorenones to form columns in the crystal. The distances between the faces of both portions indicate that interactions occur between the gold atoms, rich in electronic density, and the nitroaromatic portion of the electron acceptor. The difference between them stems from the greater complexity of the... 

Not only 2,4,7-trinitro-9-fluorenone (TNF) but also other electron acceptors, for example, TCNQ, 1,2,4,5-tetracyanoben-zene, the enantiomers of 2-(2,4,5,7-tetrani-tro-9-fluorenylideneaminooxy)-propionic acid (TAPA) or 2,4,5,7-tetranitro-9-fluore-none, and derivatives of the latter one, are effective in this type of mesophase induction [50]. In particular, a TNF derivative carrying two hexadecanoyl side chains (2,4,7-trinitrofluorenylidene-9-malonic acid bis(hexadecyl) ester) is remarkable because of the induction of a nematic columnar type (Ncoi) mesophase with hexakispen-... 

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