TY - JOUR
T1 - Fusing phthalocyanine and porphyrin together
T2 - Unprecedented co-planar ring-fused diazaphthalocyaninato-porphyrin dimers
AU - Wang, Kang
AU - Qi, Dong Dong
AU - Mack, John
AU - Wang, Hai Long
AU - Li, Wen Jun
AU - Bian, Yong Zhong
AU - Kobayashi, Nagao
AU - Jiang, Jian Zhuang
PY - 2012
Y1 - 2012
N2 - An unprecedented ring-fused co-planar diazaphthalocyaninato-porphyrin dimer H 4{[(DAPc(OC 4H 9) 6] [TC1PP]} (where DAPc (OC 4H 9) 6is the dianion of 2,3,9,10,16,17-hexa (butyloxy)-22,25-diazaphthalocyanine, and TC1PP is the dianion of 5,10,15,20-tetra(4-ch1oro)porphyrin) (1) was synthesized by mixed cyclic tetramerization of 5,10,15,20-tetrakis(4-chlorophenyl)-2′,3′-dicyanopyrazino[2,3-β] porphyrin with 4,5-di(butyloxy)phthalonitrile in the presence of lithium in refluxing n-pentanol followed by treatment with acetic acid. Reaction of the metal free dimer with Zn(OAc) 2·2H 2O in DMF and toluene led to the isolation of a bimetallic zinc(II) complex Zn 2{[(DAPc (OC 4H 9) 6] [(TClPP)]} (2). The binuclear and mixed tetrapyrrole ring nature of the structure was clearly demonstrated by a series of characterization methods including mass spectrometry and NMR spectroscopy. The Q band region of the electronic absorption and magnetic dichroism (MCD) spectra provide evidence for significant intramolecular interaction between the phthalocyanine and porphyrin chromophores. Theoretical calculations provide further support for this.
AB - An unprecedented ring-fused co-planar diazaphthalocyaninato-porphyrin dimer H 4{[(DAPc(OC 4H 9) 6] [TC1PP]} (where DAPc (OC 4H 9) 6is the dianion of 2,3,9,10,16,17-hexa (butyloxy)-22,25-diazaphthalocyanine, and TC1PP is the dianion of 5,10,15,20-tetra(4-ch1oro)porphyrin) (1) was synthesized by mixed cyclic tetramerization of 5,10,15,20-tetrakis(4-chlorophenyl)-2′,3′-dicyanopyrazino[2,3-β] porphyrin with 4,5-di(butyloxy)phthalonitrile in the presence of lithium in refluxing n-pentanol followed by treatment with acetic acid. Reaction of the metal free dimer with Zn(OAc) 2·2H 2O in DMF and toluene led to the isolation of a bimetallic zinc(II) complex Zn 2{[(DAPc (OC 4H 9) 6] [(TClPP)]} (2). The binuclear and mixed tetrapyrrole ring nature of the structure was clearly demonstrated by a series of characterization methods including mass spectrometry and NMR spectroscopy. The Q band region of the electronic absorption and magnetic dichroism (MCD) spectra provide evidence for significant intramolecular interaction between the phthalocyanine and porphyrin chromophores. Theoretical calculations provide further support for this.
KW - Conjugated dimer
KW - Mixed binuclear
KW - Phthalocyanine
KW - Porphyrin
KW - Tetrapyrrole
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M3 - Article
AN - SCOPUS:84865602404
VL - 28
SP - 1779
EP - 1789
JO - Chinese Journal of Inorganic Chemistry
JF - Chinese Journal of Inorganic Chemistry
SN - 1001-4861
IS - 9
ER -