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• W283267070 abstract "Aggregation is usually depicted as a coplanar association of rings progressing from monomer to dimer and higher order complexes. Tetrapyrazinoporphyrazine macrocycles tend towards higher aggregation compared to phthalocyanine molecules. 1 These problems are usually solved through introduction of optimal substituents onto the periphery of the tetrapyrazinoporphyrazine core that suppress the aggregation, which resulted in various applications such as chemical sensor, 2 catalyst, 3 etc. 2,3-Dicyanopyrazines for tetramerization (tetrapyrazinoporphyrazines) are usually built up through condensation of α-diketones and diaminomaleonitrile, enabling peripheral substitutions typically not available for phthalocyanines. 4 We have studied the syntheses of functional dye materials based on 2,3-dicyanopyrazine chromophores, and correlated their physical properties with structure. 5 In this paper, We designed and synthesized metal and metal-free tetrapyrazinoporphyrazines derived from 2,3-dicyanopyrazine derivatives. The 1-(4-bromophenyl)-2-(4-tert-butylphenyl)ethan-1,2dione was synthesized by a method described in the literature. 6 Using L-proline as a promoter, the coupling of 1-(4bromophenyl)-2-(4-tert-butylphenyl)ethan-1,2-dione with morpholine (1.5 eq) in DMSO gave 1-(4-morpolinophenyl)2-(4-tert-butylphenyl)ethan-1,2-dione in 56% yield. The tetrapyrazinoporphyrazine precursor (2) was synthesized from reaction of the unsymmetrical a-diketone (1) and 2,3diaminomaleonitrile. 7 Tetrapyrazinoporphyrazine magnesium complexes were synthesized from 2,3-dicyanopyrazine derivatives (2) using freshly prepared solutions of magnesium butoxide in nbutanol. 8 The corresponding metal-free derivatives were obtained by treatment with p-toluenesulfonic acid. Copper complexes were successfully synthesized using excess cuprous chloride and DBU (1,8-diazabicyclo[5,4,0]-7-undecene) as a catalyst in o-dichlorobenzene at reflux. The synthetic route of this work is summarized in Scheme 1. The ground state electronic spectra of the metal complexes showed characteristic absorption in the Q-band region at 665 nm for 3 and 669 nm for 4. 9 The metal-free phthalocyanine" @default.
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• W283267070 date "2008-10-20" @default.
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• W283267070 title "Synthesis and Aggregation Behavior of Novel Tetrapyrazino-porphyrazine Derivatives Containing Morpholine and tert-Butyl Group" @default.
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• W283267070 doi "https://doi.org/10.5012/bkcs.2008.29.10.1885" @default.
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