On the basis o the charge transfer process of the complexes, the photoemission and the electronic conduction of the complexes between cesium and pyrene derivatives, tetranitropyrene (TNO2P), tetrachloropyrene (TClP), tetrabromopyrene (TBrP) and tetracyanopyrene (TCNP) have been measured. A strong increase in the quantum yield of photoemission, from 10−3–10−4 to 10−1–102, resulting from the formation of the complexes, has been found. The promotion may take place by means of an electron transfer from cesium metal to a partner molecule; [Cs+] [Aromatics−]. The assumption is supported by the findings concerning electron spin resonance absorption and charge-transfer spectra. The electrical resistivity of the complexes, ρ at 15°C of pyrene-Cs=2.1×104 Ωcm., (TClP)-Cs=8Ωcm., (TBrP)-Cs=1.6×101 Ωcm., (TNO2P)-Cs=2×106 Ωcm. and (TCNP)-Cs=6×105 Ωcm., is strongly affected by the contribution of the, dative-bond character of the complexes.

I Hyakunincho, Shinjuku-ku, Tokyo 160, Japan Preparation of 1 -azabenz[de]anthrone (27) was carried out by making use of a German Patent reaction. An improved procedure gave (27) easily and rapidly. Compound (27) underwent self-condensation via a zinc-catalysed method or an alkali-fusion procedure. The zinc-catalysed condensation product was separated into four isomers; 3,12-diazatetrabenzo[a,cd,j,lm]perylene ( 7 ) , 3,15-diazabenzo[rst]phenanthro[l,l O,9-cdelpentaphene (4), 5,17-diazadibenzo[a,rst] naphtho[8,1,2-cde] pentaphene (3), and 5,1O-diazabenzo[rst]phenaleno[l,2,3-de]pentaphene (6). The major component was (3). The reduced product after alkali-fusion condensation of (27) was separated into four isomers; ( 7 ) , (3), (6), and 5,14-diazadinaphtho[l,2,3-cd: 1 ',2',3'-lm]perylene ( 2 ) . The major component was ( 2 ) .The structures of the isomers were assigned from their oxidation products, m.p., u.v.-visible, i.r., and mass spectra. According to our assignments, (6) and possibly 5,14-diazatetrabenzo-[a,cd,lm,o] perylene (1 0) are new structural isomers of fused nanocyclic compounds whose parent aromatic hydrocarbons have not been prepared, though (10) has not actually been isolated.

The electron and hole drift mobilities in highly pure perylene single crystals were measured using a conventional time-of-flight method. Observed values were 0.017 f 0.001 cm2/V sec for electrons and 0.02 -& 0.003 cm2/V sec for holes a t room temperature. The mobilities increased with the temperature between 296"-353 O K with an activation energy of 0.20 eV for electrons.Taking a fluctuation of transfer integrals and a stabilization of electron energy due to the excimer-like excess electron state into consideration, the fairly good agreement between the calculated and measured values of mobility has been obtained.

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The crystals of naphthanthrone(C19H10O) are orthorhombic, with the P212121 space group and these lattice constants: a=17.345(17), b=3.973(13), c=17.392(14) Å, and Z=4. The structure was solved by the Patterson method and refined by a block-diagonal least-squares program to give an R-value of 0.085 on the basis of the 897 observed reflections collected by Weissenberg photographs. The molecule is planar within the limits of experimental error and has an approximate symmetry of mm. The molecules are stacked face-to-face by van der Waals forces along the b-axis. The interplanar spacing is 3.50 Å.

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Electron impact mass spectra were measured for five isomers of pyridinobenzanthrones and three isomers of benzobenzanthrones. The fragmentation pattern and intensity of M", [M -HI', [ M -CO]'+, [M -CO -H(or 2H)I" and [ M -CO -HCN]" (i = 1, 2) ions indicated remarkable differences and very interesting features according to the isomers with or without nitrogen and condensation positions of a pyridino or benzo ring to the benzanthrone skeleton. Further, the competition of decompositions through [ M -HI', [M -CO]" or [M -HCN] + * ions was confirmed by the observation of metastable ions and the appearance energies of fragment ions. Interesting observations from these results were expulsion of an H atom in close proximity to the area around an O=C group, a weak bonding interaction between sp2 C-H and an O=C group, inducing specific hydrogen rearrangement, and characteristic charge localization on heteroatoms.