Chromogenic Properties of 3,3'-Bis(1-n-octyl-2-methylindol-3-yl)phthalide with Color Developers in Alcohol

doi:10.11944/j.issn.1000-0518.2015.12.150170

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (12): 1437-1447.DOI: 10.11944/j.issn.1000-0518.2015.12.150170

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Chromogenic Properties of 3,3'-Bis(1-n-octyl-2-methylindol-3-yl)phthalide with Color Developers in Alcohol

LIU Fuyong,FENG Dan,WU Yongping,WU Jiana,DONG Chuan()

Institute of Environmental Science,Shanxi University,Taiyuan 030006,China

Received:2015-05-14 Accepted:2015-08-21 Published:2015-12-01 Online:2015-12-01
Contact: DONG Chuan
Supported by:
Supported by the National Natural Science Foundation of China(No.21175086), Talent Construction Project of Shanxi University(No.205533801001)

Abstract

Abstract:

The structures of dye 3,3'-bis(1-n-octyl-2-methylindol-3-yl)phthalide(ck-16) in coloring and decoloring states were analyzed by ¹³C NMR. The chromogenic properties of ck-16 interacted with different color developers in ethyl alcohol were studied by UV-visible spectroscopy. The composition ratio and instability constant of the complexes composed of ck-16 and the color developers were measured. Furthermore, the effect of external conditions on the absorbance at λ_max of the system was investigated. ¹³C NMR results show that the delocalized bonds formed between electron donor(N) and acceptor(O) atoms lead to ring cleavage of the phthalide to a carboxylate as a colored form. The chromogenic properties of ck-16 vary with different color developers. When the molar ratio of ck-16 to four color developers(FeCl₃, oxalic acid, CuCl₂ and salicylic acid) are all 1:1, the combination between ck-16 with Fe³⁺ is the most stable, followed by oxalic acid and Cu²⁺. Among the four color developers, the combination between ck-16 with salicylic acid is the most instable. The time has little influence on the absorbance at λ_max of ck-16/FeCl₃ and ck-16/H₂C₂O₄. However, different sensibility is observed when water is added. The ck-16/FeCl₃ fades more rapidly with water than ck-16/H₂C₂O₄, and exhibits potential application as water sensitive recording or copying materials.

Key words: fluorane, color developer, chromogenic properties, UV-Vis spectrum

LIU Fuyong, FENG Dan, WU Yongping, WU Jiana, DONG Chuan. Chromogenic Properties of 3,3'-Bis(1-n-octyl-2-methylindol-3-yl)phthalide with Color Developers in Alcohol[J]. Chinese Journal of Applied Chemistry, 2015, 32(12): 1437-1447.

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Chromogenic Properties of 3,3'-Bis(1-n-octyl-2-methylindol-3-yl)phthalide with Color Developers in Alcohol

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