Abstract
Some phthalocyanines soluble in organic solvents have been developed by peripheral introduction of substituent groups. We report a new method for preparation of the polyphenyl-substituted dicyanopyrazines based on the [2 + 4] Diels-Alder cycloaddition of the tetraphenylcyclopentadienone to an ethynyl compound. The synthesised tetrapyrazinoporphyrazinato metal complexes were characterised by UV-visible spectroscopy, MALDI-TOF-Ms (matrix-assisted laser desorption ionisation time-of-flight mass) spectroscopy, and 1H NMR spectroscopy.
References
1.
Lenzoff C.C.
, and
Lever A. P. F.
, Phthalocyanine-properties and applications , VCH , New York , 1996 , Vol. IV .
2.
Piechoki C.
,
Simon J.
,
Skoulious A.
,
Gullion D.
, and
Weber P.
, J. Am. Chem. Soc. , 1982 , 104 , 5245 .
3.
Snow A.W.
,
Barger W. R.
,
Klusty M.
,
Wohltjen H.
, and
Jarvis N. L.
, Langmuir , 1986 , 2 , 513 .
4.
Grund A.
,
Kaltbeitzel A.
,
Mathy A.
,
Schwarz R.
,
Bubeck C.
,
Vernmehren P.
, and
Hanack M.
, J. Phys. Chem. , 1992 , 96 , 7450 –4 .
5.
Okura I.
Photosensitisation of porphyrins and phthalocyanines , Taylor & Francis , 2001 .
6.
Ali H.
, and
van Lier J. E.
, Chem. Rev. , 1999 , 99 , 2379 –2450 .
7.
Smolenyak P.
,
Peterson R.
,
Nebesny K.
,
Toerker M.
,
O'Brien D.
, and
Armstrong N. R.
, J. Am. Chem. Soc. , 1999 , 12 , 8628 .
8.
Zangmeister R.A. P.
,
O'Brien D. F.
, and
Armstrong N. R.
, Adv. Funct. Mater. , 2002 , 12 , 179 –186 .
9.
Faust R.
, and
Weber C.
, J. Org. Chem. , 1999 , 64 , 2571 .
10.
Faust R.
, Eur. J. Org. Chem. , 2001 , 15 , 2797 –2803 .
11.
Pisula W.
,
Dierschke F.
, and
Müllen K.
, J. Mater. Chem. , 2006 , 16 , 4068 –4064 .
12.
Lee B.H.
, and
Jaung J. Y.
, Dyes Pigments , 2003 , 59 , 135 –142 .
13.
Wehmeier M.
,
Wagner M.
, and
Müllen K.
, Chem. Eur. J. , 2001 , 7 , 2197 –2205 .
14.
Wiesler U.M.
,
Berresheim A. J.
,
Morgenroth F.
,
Leser G.
, and
Müllen K.
, Macromolecules , 2001 , 34 , 187 –199 .
15.
Ou Z.
,
Shen J.
, and
Kadish K. M.
, Inorg Chem. , 2006 , 45 , 9569 –79 .
16.
Weitman H.
,
Schatz S.
,
Gottlieb H. E.
,
Kobayashi N.
, and
Ehrenberg B.
, Photochem. Photobiol. , 2001 , 73 , 473 –481 .
