CIESC Journal ›› 2015, Vol. 66 ›› Issue (4): 1577-1584.doi: 10.11949/j.issn.0438-1157.20141576

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Synthesis and application of soluble near-infrared absorption amino phthalocyanine dyes

ZHAO Ming, LI Jian, JI Junling, REN Qiang, WANG Chenyi, AI Baolin   

  1. Jiangsu Key Laboratory for Solar Cell Materials and Technology, School of Materials Science and Engineering, Changzhou University, Changzhou 213164, Jiangsu, China
  • Received:2014-10-22 Revised:2014-11-28 Online:2015-04-05 Published:2015-01-15


A series of soluble near-infrared absorption amino phthalocyanine dyes were synthesized with preparation of amino phthalonitriles firstly. The structure and performance of phthalocyanines were characterized by 1H NMR, Fourier transform infrared spectroscopy (FT-IR), solution test, UV-visible absorption spectroscopy (UV-Vis), thermal gravimetric analysis (TGA). The results showed that amino phthalocyanines were successfully synthesized. The solubility of amino phthalocyanines was greatly influenced by substituents, position of the substituents and metal ions. When aliphatic amine was used as the peripheral substituent at α position and Mn2+ was used as the central substituent of phthalocyanine, solubility could greatly be increased. A red-shift of the Q-band was observed when aliphatic amine and Mn2+ were introduced into phthalocyanine, mainly due to the electron-donating ability of aliphatic amine. The 3, 3', 3", 3"'-tetra-n-butyl amine manganese (Ⅱ) phthalocyanine (a-TnBAMnPc) showed Q-band peak at 870 nm in chloroform. The near-infrared absorption performance of a-TnBAMnPc in poly(methyl methacrylate) (PMMA) and waterborne polyurethane (WPU) films was investigated. For PMMA-(a-TnBAMnPc) films, the transmission at 862 nm was near 0 when the content of a-TnBAMnPc was more than 0.60%(mass). The transmission at 866 nm approached 0 with the content of a-TnBAMnPc beyond 0.40%(mass) for WPU-(a-TnBAMnPc) films.

Key words: amino phthalocyanine, solubility, absorption, near-infrared absorbing coating, phthalocyanine, film

CLC Number: 

  • O625.6

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