Development of Unimolecular Thermo-Response Dyes and Application to the Image Formation

氟染料广泛用于无碳纸和传真系统用纸的压力和热敏染料。当染料与酸（通常是酚类化合物）在加热时发生反应时，就会变色。为了在加热前保持无色，染料必须避免与酸接触。这通常会导致技术问题，并限制了有机介质（如聚合物薄膜）的使用。我们的策略利用了这样一个事实，即在加热时，中性烯丙基芳基醚通过Claisen重排产生酸性酚基团。由此产生的酚基发生分子内酸碱反应，导致内酯基团开环并着色。本课题主要研究了单分子热响应染料的发展及其在成像中的应用。项目取得的主要成果简述如下：针对染料变色性能的发展，合成了多种单分子热响应染料。对染料的合成方案进行了改进，以适应大规模制备。准备好了染料的试纸。对染料（染色前后）进行了x射线分析。用几种光谱方法对染料进行了表征。研究了单分子光反应染料的分子设计与合成。

Fluoran dyes are widely used as pressure-and heat-sensitive dyes for carbonless paper and paper for fax systems. Coloration occurs when the dyes react with acid, normally phenolic compounds, upon heating. To retain the colorless form before heating, the dyes must be protected from contact with acid. This often causes technical problems and restricts the use of organic medium such as polymer films. Our strategy utilized the fact that upon heating, neutral allyl aryl ethers generate acidic phenol groups by the Claisen rearrangement. Phenol groups thus generated undergo intramolecular acid-base reaction, which in turn causes the ring opening of the lactone groups and the coloration.In this project, we investigated the development of the unimolecular thermo-response dyes and application of the dyes to Image formation. The main results obtained in the project are briefly outlined below :1. Various unimolecular theromo-response dyes were synthesized aiming at the development of the color variation for the dyes.2. Syntheic scheme for the dyes were modified for the large-scale preparation.3. Test papers for the dyes were prepared.4. X-ray analyzes of the dyes (before and after the coloration) were performed.5. Characteristics of the dyes were carried out by several spectroscopic methods.6. Molecular design and syntheses of unimolecular light-response dyes were studied.