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 their 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-iiminoisoindoline, 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

A1166 A1166 B1353 B1353 B1334 B1334
C1163 C1163 D2189 D2189 D1610 D1610
D3963 D3963 D2079 D2079 D1983 D1983
D2237 D2237 H0691 H0691 H0813 H0813
M1379 M1379 N0524 N0524 N0566 N0566
P1071 P1071 P0404 P0404 P1070 P1070
T0988 T0988 T1402 T1402
A1166 4-Aminophthalonitrile
B1353 4-Butoxyphthalonitrile
B1334 4-tert-Butylphthalonitrile
C1163 4-(4-alpha-Cumylphenoxy)phthalonitrile
D2189 4,5-Dichlorophthalonitrile
D1610 2,3-Dicyanohydroquinone
D3963 4,5-Difluorophthalonitrile
D2079 1,3-Diiminoisoindoline
D1983 4-(2',6'-Dimethylphenoxy)phthalonitrile
D2237 4-Dodecyloxyphthalonitrile
H0691 4-Hexyloxyphthalonitrile
H0813 4-Hydroxyphthalonitrile
M1379 4-Methylphthalonitrile
N0524 4-Nitrophthalonitrile
N0566 3-Nitrophthalonitrile
P1071 4-Pentyloxyphthalonitrile
P0404 Phthalonitrile
P1070 4-Propoxyphthalonitrile
T0988 1,2,4,5-Tetracyanobenzene
T1402 Tetrafluorophthalonitrile

Naphthalonitriles

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

Others

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

Phthalocyanines

P0887 P0887 C2427 C2427 P1005 P1005
P1006 P1006 T1256 T1256 P1049 P1049
P0973 P0973 H1194 H1194 P0774 P0774
P0766 P0766 P1018 P1018 P0355 P0355
P1795 P1795 C1167 C1167 P0996 P0996
P0655 P0655 P1628 P1628 S0363 S0363
P1024 P1024 P0997 P0997 P0767 P0767
P0887 Cobalt(II) Phthalocyanine
C2427 Copper(II) 2,3,9,10,16,17,23,24-Octafluorophthalocyanine (purified by sublimation)
P1005 Copper(II) Phthalocyanine (alpha-form)
P1006 Copper(II) Phthalocyanine (beta-form)
T1256 Copper(II) 2,9,16,23-Tetra-tert-butylphthalocyanine
P1049 Dilithium Phthalocyanine
P0973 Disodium Phthalocyanine
H1194 1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyanine Copper(II) (purified by sublimation)
P0774 Iron(II) Phthalocyanine
P0766 Lead(II) Phthalocyanine
P1018 Magnesium(II) Phthalocyanine
P0355 Phthalocyanine
P1795 Phthalocyanine (purified by sublimation)
C1167 Phthalocyanine Chloroaluminum
P0996 Phthalocyanine Silicon Dichloride
P0655 Pigment Blue 15
P1628 Pigment Blue 15 (purified by sublimation)
P0660 Pigment Green 7
S0363 Silver(I) Phthalocyanine
P1024 Tin(II) Phthalocyanine
P0997 Tin(IV) Phthalocyanine Dichloride
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 [DOI]; M. Chigane, Kagaku To Kogyo (Osaka), 1995, 69, 26.
4) W. R. Barger, A. W. Snow, H. Wohltjen, N. L. Jarvis, Thin Solid Films, 1985, 133, 197 [DOI]; A. W. Snow, W. R. Barger, M. Klusty, H. Wohltjen, N. L. Jarvis, Langmuir, 1986, 2, 513 [DOI].
5) K. Sakamoto, Shikizai Kyokaishi, 2002, 75, 286.


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