Phthalonitriles & Naphthalonitriles

Phthalocyanines (Pc) are the general term for compounds that contain the tetrabenzotetraazaporphine (H2-Pc) ring, which is the porphyrin analog and metal phthalocyanines (M-Pc). M-Pc has attractive physical properties associated with there structures, and this has led to a broad spectrum of studies being done on synthetic methods and properties. Amongst the many synthetic methods, ones using 1,2-dicyanobenzene or 1,3-diiminoisoindoline, are the most common, since these methods produce the products in high purity.1) M-Pc possesses a large delocalized π electron system due to the tetraazaporphine ring, which leads to interesting and useful photochemical properties. The photochemical and photophysical properties of these systems have been studied extensively, and some of these compounds have been put to practical use. The weather-resistant blue and green pigments are one example, and in other examples, the photoelectric properties have been applied to optical memory disks, luminescent devices and solar batteries. M-Pc is also utilized as carrier-generation-layer of electrophotographic photoconductor.2) Furthermore, M-Pc has redox properties which find use as an electrochromic material3), which results in a reversible discoloration phenomenon caused by changing the applied electric potential. M-Pc is also used as a deodorant and antibacterial agent by selection of the appropriate central metals and the making of pendant-type polymers.1) In other examples, M-Pc has uses in M-Pc derivative sensor4), liquid crystal5), photochemical therapy for cancer and many others. M-Pc is the functional material of the 21st-Century, and more is anticipated upon further research and development.

Phthalonitriles

Naphthalonitriles

Others

Phthalocyanines

Phthalonitriles

T0988 T0988 D2079 D2079 D1610 D1610
N0566 N0566 D2189 D2189 D1983 D1983
C1163 C1163 A1166 A1166 B1353 B1353
D2237 D2237 H0691 H0691 H0813 H0813
M1379 M1379 P1071 P1071 P1070 P1070
N0524 N0524 B1334 B1334 P0404 P0404
T1402 T1402
T0988 1,2,4,5-Tetracyanobenzene
D2079 1,3-Diiminoisoindoline
D1610 2,3-Dicyanohydroquinone
N0566 3-Nitrophthalonitrile
D2189 4,5-Dichlorophthalonitrile
D1983 4-(2',6'-Dimethylphenoxy)phthalonitrile
C1163 4-(4-alpha-Cumylphenoxy)phthalonitrile
A1166 4-Aminophthalonitrile
B1353 4-Butoxyphthalonitrile
D2237 4-Dodecyloxyphthalonitrile
H0691 4-Hexyloxyphthalonitrile
H0813 4-Hydroxyphthalonitrile
M1379 4-Methylphthalonitrile
P1071 4-n-Pentyloxyphthalonitrile
P1070 4-n-Propoxyphthalonitrile
N0524 4-Nitrophthalonitrile
B1334 4-tert-Butylphthalonitrile
P0404 Phthalonitrile
T1402 Tetrafluorophthalonitrile

Naphthalonitriles

N0578 N0578 D2009 D2009 D2282 D2282
D2434 D2434 D2027 D2027 D1977 D1977
B1390 B1390
N0578 1,2-Naphthalenedicarbonitrile
D2009 1,3-Diiminobenz[f]isoindoline
D2282 2,3-Dibromo-6,7-dicyanonaphthalene
D2434 2,3-Dicyano-1,4-dihydroxy-5-nitronaphthalene
D2027 2,3-Dicyano-6-nitronaphthalene
D1977 2,3-Dicyanonaphthalene
B1390 6-Bromo-2,3-dicyanonaphthalene

Others

T1472 T1472 D2148 D2148 D2281 D2281
D1751 D1751 A1292 A1292 D2026 D2026
D2270 D2270 D2271 D2271 D2269 D2269
P1218 P1218
T1472 1,4,5,6-Tetrahydro-5,6-dioxo-2,3-pyrazinedicarbonitrile
D2148 1,4-Diamino-2,3-dicyano-9,10-anthraquinone
D2281 2,3-Dicyano-5-methylpyrazine
D1751 2,3-Dicyanopyrazine
A1292 2-Amino-4,5-dicyano-1H-imidazole
D2026 4,5-Dicyanoimidazole
D2270 5,6-Diamino-2,3-dicyanopyrazine
D2271 5,6-Dichloro-2,3-dicyanopyrazine
D2269 5-Amino-6-chloro-2,3-dicyanopyrazine
P1218 Pyridine-2,3-dicarbonitrile

Phthalocyanines

T1256 T1256 P0887 P0887 P0774 P0774
P1018 P1018 P0355 P0355 P1795 P1795
C1167 C1167 P1005 P1005 P1006 P1006
P1049 P1049 P0766 P0766 P0996 P0996
S0363 S0363 P1024 P1024 P0997 P0997
P0655 P0655 P0973 P0973 P0767 P0767
T1256 4,4',4'',4'''-Tetra-tert-butylphthalocyanine Copper
P0887 Cobalt(II) Phthalocyanine
P0774 Iron Phthalocyanine
P1018 Magnesium Phthalocyanine
P0355 Phthalocyanine
P1795 Phthalocyanine (purified by sublimation)
C1167 Phthalocyanine Chloroaluminum
P1005 Phthalocyanine Copper (alpha-form)
P1006 Phthalocyanine Copper (beta-form)
P1049 Phthalocyanine Dilithium (contains ca. 20% 1-Pentanol)
P0766 Phthalocyanine Lead
P0996 Phthalocyanine Silicon Dichloride
S0363 Phthalocyanine Silver
P1024 Phthalocyanine Tin(II)
P0997 Phthalocyanine Tin(IV) Dichloride
P0655 Pigment Blue 15
P0660 Pigment Green 7
P0973 Sodium Phthalocyanine
P0767 Zinc Phthalocyanine

Literature

1)N. Kobayashi, Kagaku To Kogyo (Tokyo), 1999, 52, 968; N. Kobayashi, Senryo To Yakuhin, 1996, 41, 312.
2)D.Wohrle, M. Kaneko, Yuki Gosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.), 1987, 45, 837; H. Shirai,
K. Hanabusa, Hyomen, 1987, 25, 422.
3)B. Schumann, D.Wohrle, N. I. Jaeger, J. Electrochem. Soc., 1985, 132, 2144; M. Chigane, Kagaku To Kogyo (Osaka), 1995, 69, 26.
4)W. R. Barger, A. W. Snow, H. Wohltjen, L. Jarvis, Thin Solid Films, 1985, 133, 382; A. W. Snow, W. R. Barger,
M. Klusty, Langmuir, 1986, 2, 513.
5)K. Sakamoto, Shikizai, 2002, 75, 286.


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