The two indolocarbazoles 2 and 4 were synthesized via the reductive ring closure of dinitrodiphenylbenzenes with triethylphosphite as reducing agent in a high boiling solvent. The electrochemical behaviour of the title systems is discussed.
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Present address: BASF AG, D-67056 Ludwigshafen, FRGThe synthesis and the optical properties of the novel polymer polyphenothiazinobisthiazole (PPT) are described. The design of this polymer was planned taking into consideration several aspects that were anticipated to lead to a material with an enhanced nonlinear optical susceptibility Monomer 16 was prepared in a five-step synthesis starting from N-dodecyl-3,7-diaminophenothiazin (11). 16 was reacted with terephthaloyl chloride to yield the precursor polyamide 17.This precursor polyamide was subjected to a thermal cyclization at 300 OC under vacuum leading to the title polymer PPT (18).PPT shows UVIvis absorption maxima at 1 =282 nm,305 nm and 463 nm.The macroscopic nonlinear optical suscepti-bility~'~)(-3w; w, w, w ) of a thin film ofPPTwas determined with a third harmonic generation (THG) technique at a fundamental laser wavelength 1,. = 1064 nm. The results show that PPT exhibits nonlinear optical properties comparable to those of poly-p-phenylenevinylene (PPV).
The syntheses of 6 and ?, starting from 3,6-dichloro-2,5-bis(2-EPR measurements on the radical cations derived from 6 and thioanisido)-1,4-benzoquinone (4), are reported. The solid-state 7 both suggest a planarized conformation of these species. Oxiconformations of 6 and ? are elucidated by X-ray structure dation 01 6 with strong oxidants leads quantitatively to the analysis, and the cyclovoltammetric investigation of 6 and 7 quinoid triphenodithiazine 8, whereas the charge-transfer in solution shows low and reversible oxidation half-waves for complex formed between 7 and DDQ exhibits semiconducting both compounds. The relatively high oxidation potentials of properties. 7 compared to 6 are related to their conformational features.Triphenodithiazine 2 has recently attracted attention as a model compound for poly(phen0thiazine) (1)['-31. This ladder polymer is supposed to possess high intrinsic conductivity and shows non-linear optical activityL4-']. The two most important features of this system are the rigid ladder structure that allows for extended n-conjugation and the presence of heteroatoms, which should give rise to low oxidation potentials and high donor ability. 1 is a hetero analog of a ladder-type arylenemethideL8]. The parent compound 7,14-dihydrotriphenodithiazine (3) has been synthesized by starting from N,N'-diphenyl-p-phenylenediamine which is thionated with elemental sulfur and a trace of iodine at elevated temperatures in a high-boiling solventL2'. Unfortunately, the product shows a very low solubility, which seriously inhibits a full spectroscopic characterization and further chemical transformations. In order to obtain detailed information on the chemical and electrochemical properties of 7,14-dihydrotriphenodithiazine and triphenodithiazine, we have worked out a straightforward synthesis of a soluble derivative.
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