3,3-双(N-辛基-2-甲基吲哚)邻苯二甲内酯荧烷在乙醇溶液中的显色性能

doi:10.11944/j.issn.1000-0518.2015.12.150170

摘要/Abstract

摘要：

测试了3,3-双(N-辛基-2-甲基吲哚)邻苯二甲内酯荧烷(ck-16)在显色前后的¹³C NMR谱图,揭示了其显色前后的结构变化及其显色机理。利用紫外可见吸收光谱法研究了ck-16在乙醇溶液中与不同显色剂作用后的光谱性质,测定了其与常用显色剂间的络合比和不稳定常数,并进一步研究了外界条件的改变对ck-16在乙醇溶液中与特定显色剂作用后显色性能的影响。研究发现,亲电阳离子进攻ck-16荧烷分子的苯酞环,使苯酞环断裂,推电子的N原子和吸电子的羰基O原子之间建立π电子迁移通道使分子显色。在乙醇介质中,ck-16与不同显色剂作用后具有不同的显色效果;对路易斯酸和有机弱酸这两类显色剂而言,ck-16与所测的四种显色剂(FeCl₃、草酸、CuCl₂、水杨酸)均以1:1的形式络合,ck-16与Fe³⁺的不稳定常数最小,结合最稳定,草酸其次,与Cu²⁺的相近,ck-16与水杨酸的结合最弱;在乙醇中,放置时间对ck-16/FeCl₃和ck-16/H₂C₂O₄两个体系的吸光度影响不大,但两体系表现出随水含量变化不同的敏感性,ck-16/FeCl₃体系具有比ck-16/H₂C₂O₄体系更为灵敏和快速的水致褪色性能。

关键词: 荧烷染料, 显色剂, 显色性能, 紫外可见光谱

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

刘付永, 冯丹, 武永平, 吴佳娜, 董川. 3,3-双(N-辛基-2-甲基吲哚)邻苯二甲内酯荧烷在乙醇溶液中的显色性能[J]. 应用化学, 2015, 32(12): 1437-1447.

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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