The Crystal and Molecular Structure of Naphthanthrone

Fujisawa, Shoji; Oonishi, Isao; Aoki, Junji; Iwashima, Satoshi

doi:10.1246/bcsj.49.3454

Cited by 7 publications

(5 citation statements)

References 5 publications

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“…40 (1)A [(I [7,8,1,2-defg]anthrone (Fujisawa et al, 1976) lies between the observed values for (I) and (II).…”

Section: C(6)-c(16)-c(14)supporting

confidence: 59%

See 1 more Smart Citation

The structure of 7H-benzo[hi]chrysen-7-one (α form)

Fujisawa¹,

Sato²,

Saito³

1981

Acta Crystallogr Sect B

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Crystals of the title compound, C21H~20, are monoclinic, space group P21/c, with the lattice constants a = 7.663(1), b = 8.299(1), c = 21.865 (2)/k, fl = 102.61 (1) ° and Z = 4. The structure was solved by the direct method and refined by a full-matrix leastsquares program to an R value of 0.059 on the basis of 1301 reflections collected on an automated four-circle diffractometer. The molecules are slighly distorted from a planar structure owing to the overcrowding around the O atom. The structure consists of pairs of molecules and it is disordered. There are two pairs with different overlapping modes and they are arranged randomly with different populations. The interplanar distances in the dimer pairs are 3.47 (1) and 3.52 (3) respectively.

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“…40 (1)A [(I [7,8,1,2-defg]anthrone (Fujisawa et al, 1976) lies between the observed values for (I) and (II).…”

Section: C(6)-c(16)-c(14)supporting

confidence: 59%

“…In contrast, naphth [7,8,1,2-defg]anthrone (Fujisawa, Oonishi, Aoki & Iwashima, 1976) does not exhibit such a dimeric structure.…”

Section: C(6)-c(16)-c(14)mentioning

confidence: 96%

The structure of 7H-benzo[hi]chrysen-7-one (α form)

Fujisawa¹,

Sato²,

Saito³

1981

Acta Crystallogr Sect B

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“…The synthesis and purification of NT were performed according to the previously reported procedure (1). As solvents we used methanol, ethanol, and their deuterated compounds, C 2 H 5 OD, CH 3 OD and CD 3 OD: non-deuterated solvents were purchased from Koso Chemical, Tokyo, Japan, and the deuterated ones from Wako Pure Chemical Industries, Osaka, Japan, and used without purification.…”

Section: Methodsmentioning

confidence: 99%

“…Naphthanthrone, 6H-benzo[cd]pyren-6-one, (NT) is a penta-cyclic mono ketone and synthesized by glycerol condensation of pyrene (1). Its separation and purification are, however, so laborious that only a few studies of its spectroscopic properties exist in the literature.…”

Section: Introductionmentioning

confidence: 99%

FLUORESCENCE ENHANCEMENT OF 6H-BENZO[cd]PYREN-6-ONE (NAPHTHANTHRONE): EFFECTS OF CONCENTRATION, LIGHT INTENSITY, AND DEUTERATION OF SOLVENTS

Yagishita

Ohshima

2010

GPOL

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Fluorescence of naphthanthrone, 6H-benzo[cd]pyren-6-one, in degassed organic solution increases by a factor of 10-100 on strong irradiation and the spectrum is blueshifted. To clarify the mechanism of the fluorescence enhancement, we investigated effects of intensity of irradiation, deuteration of solvents, and concentration of naphthanthrone on the enhancement. The fluorescence was more rapidly enhanced with stronger irradiation, though there was a latent period of several minutes. The enhancement was, however, reduced to 30-70% by deuteration of the solvents. The spectra of enhanced fluorescence showed more defined vibrational structure and larger blue-shift as the concentration was decreased from 10 −4 to 10 −6 M. These experimental results were interpreted on the basis of the associative complex model: the association of naphthanthrone with a solvent molecule proceeds step-wisely in a solvent cage by several times of excitation and undergoes kinetic isotope effects. At lower concentrations, the movement of the associative complex is more strongly suppressed, leading to enhanced fluorescence spectra with clearer vibrational structure and larger blue-shift.

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“…Furthermore, neither the expected conventional McMurry reaction products, ( E )- and ( Z )-7-(7 H -benz[ de ]anthracenylidene)-7 H -benz[ de ]anthracene (( E )- 7 and ( Z )- 7 ), nor their electrocyclization−aromatization C 34 H 16 products, dibenzo[ fg , ij ]phenanthro[2,1,10,9,8,7- pqrstuv ]pentaphene ( 8 ) and perylo[3,2,1,12- pqrab ]perylene ( 9 ), were found in the reaction mixture. An analogous low-valent titanium-induced reductive “dimerization” of 4 afforded the overcrowded chiral LPAH dibenzo[ jk , uv ]dinaphtho[2,1,8,7- defg ;2‘,1‘,8‘,7‘- opqr ]pentacene ( 10 ) − in 1.3% yield. The major product of the reaction was 6 H -benzo[ cd ]pyrene 25 (37% yield).…”

mentioning

confidence: 99%

Large PAHs by Reductive Peri−Peri “Dimerization” of Phenalenones

and

Agranat

1999

Org. Lett.

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Reactions of phenalenone (2), benzanthrone (3), and naphthanthrone (4) with a low-valent titanium reagent (TiCl4/LiAlH4/THF) gave peropyrene (1), tetrabenzo[a,cd,j,lm]perylene (6), and dibenzo[jk,uv]dinaphtho[2,1,8,7-defg;2‘,1‘,8‘,7‘-opqr]pentacene (10), respectively. The syntheses of the LPAHs 6 and 10 were regioselective. An unsymmetrical pathway of reductive peri−peri “dimerization” of the phenalenones leading to peropyrene-type LPAHs was proposed. Ab initio DFT B3LYP/6-311G** calculations indicated that D 2 h -1, the most stable conformation, resembles the Clar picture of 1.

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The Crystal and Molecular Structure of Naphthanthrone

Cited by 7 publications

References 5 publications

The structure of 7H-benzo[hi]chrysen-7-one (α form)

The structure of 7H-benzo[hi]chrysen-7-one (α form)

FLUORESCENCE ENHANCEMENT OF 6H-BENZO[cd]PYREN-6-ONE (NAPHTHANTHRONE): EFFECTS OF CONCENTRATION, LIGHT INTENSITY, AND DEUTERATION OF SOLVENTS

Large PAHs by Reductive Peri−Peri “Dimerization” of Phenalenones

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