超声波辐射下光致变色螺吡喃类化合物的快速合成

在超声辐射条件下,以1,3,3-三甲基-2-亚甲基吲哚啉和5-硝基水杨醛为原料,以甲醇为溶剂,合成了光致变色化合物1,3,3-三甲基-6'-硝基螺吲哚啉苯并吡喃,以甲醇为溶剂,在有机碱六氢吡啶存在下,将1-羟乙基-2,3,3-三甲基吲哚啉碘化物和5-硝基水杨醛通过"一锅煮"的方式,合成了光致变色化合物1-羟乙基-3,3-二甲基-6'-硝基螺吲哚啉苯并吡喃。实验证实,超声辐射显著的加快了螺吡喃类化合物的合成过程。     

超声波辐射下光致变色螺吡喃类化合物的快速合成

在超声辐射条件下,以1,3,3-三甲基-2-亚甲基吲哚啉和5-硝基水杨醛为原料,以甲醇为溶剂,合成了光致变色化合物1,3,3-三甲基-6'-硝基螺吲哚啉苯并吡喃,以甲醇为溶剂,在有机碱六氢吡啶存在下,将1-羟乙基-2,3,3-三甲基吲哚啉碘化物和5-硝基水杨醛通过"一锅煮"的方式,合成了光致变色化合物1-羟乙基-3,3-二甲基-6'-硝基螺吲哚啉苯并吡喃。实验证实,超声辐射显著的加快了螺吡喃类化合物的合成过程。     

吲哚啉苯并吡喃磺酸的合成及水性光致变色墨水的配制

由5-硝基水杨醛和吲哚啉合成了6-硝基-1',3',3'-三甲基-5'-磺酸基吲哚啉苯并吡喃光致变色材料,进行了红外、紫外和质谱等表征,研究了其在氯仿和乙醇溶液中的光致变色行为,对其光致变色机理进行了探讨。配制了具有绿色环保、成本较低的水溶性光致变色墨水。     

含BOC保护基团的螺吡喃类化合物的合成及其光致变色性能的研究

合成了5-[N-（叔丁氧甲酰基）氨基]-1,3,3-三甲基-6′-硝基吲哚啉螺吡喃（BOCSPI）和5-[N-（叔丁氧甲酰基）氨基]-1,3,3-三甲基-6′-硝基-8′-甲氧基吲哚啉螺吡喃（BOCSPII）两种光致变色化合物,采用紫外-可见光谱法研究了其在溶液和以不同质量比掺杂在聚甲基丙烯酸甲酯（PMMA）膜中的光致变色性能.研究表明螺吡喃的高掺杂量不利于其开环和闭环态的转化,BOCSPII分子中的甲氧基有利于有色开环体的部花菁的稳定.     

N-甲基螺嗯嗪光致变色染料的合成及其光致变色性质研究

以1,3,3-三甲基-2-亚甲基吲哚啉和1-亚硝基-2-萘酚为原料合成了N-甲基-3,3-二甲基螺吲哚啉-2,3’[3H]萘并[2,1-b][1,4]嗯嗪,对其进行了紫外和红外光谱以及元素分析,并对其光致变色性质以及主要影响因素温度、溶剂和pH进行了研究。结果表明,该化合物具有良好的光致变色性和一定的酸致变色性;温度、溶剂极性和pH对其光致变色性有不同程度的影响。     

2,3,3-三甲基-3H-吲哚甲基化新工艺的研究——相转移催化在N-甲基化反应中的应用

1,3,3-三甲基-2-亚甲基吲哚啉是合成阳离子染料和光致变色物质的重要中间体。本文以三乙基苄基氯化铵(TEBA)作相转移催化剂,对2,3,3-三甲基-3H-吲哚的N-甲基化进行研究,通过正交实验,找到了甲基化的最佳条件,使1,3,3-三甲基-2-亚甲基吲哚啉的实际收率稳定在90～92％,含量96～99％。从而为工业生产高质量1,3,3-三甲基-2-亚甲基吲哚啉提供了新的途径。     

1,3,3-三甲基-2-亚甲基吲哚啉的分光光度测定

1,3,3-三甲基-2-亚甲基吲哚啉是合成某些阳离子染料以及光致变色螺环化合物的重要中间体,应用范围较广。但有关它的分析测定方法,迄今仍未见有报导。为此,我们研究了用分光光度法测定1,3,3-三甲基-2-亚甲基吲哚啉含量的方法。1,3,3-三甲基-2-亚甲基吲哚啉通常采用甲基异丙基酮通过费歇尔吲哚合成得2,3,3-三甲基-3H-吲哚,再甲基化而得。     

吲哚啉螺吡喃化合物光致变色性能的研究及在生物细胞成像中的应用

吲哚啉螺吡喃是一种重要的光致变色化合物,由于具有良好的变色回复性、抗疲劳性而得到广泛的关注.本文合成了1′-羟乙基-3′,3′-二甲基吲哚啉- 6-硝基螺吡喃,研究了该化合物在紫外-可见光交替照射下紫外吸收强度的变化,并测试了光照前后化合物的荧光光谱.在开环态时,化合物具有优良的荧光性能,可以成功应用于细胞成像,在活细胞中可获得清晰的荧光成像图,同时也可以发挥螺吡喃光致变色可循环、耐疲劳等优势.     

N-甲基螺噁嗪光致变色染料的合成及其光致变色性质研究

以1,3,3-三甲基-2-亚甲基吲哚啉和1-亚硝基-2-萘酚为原料合成了N-甲基-3,3-二甲基螺吲哚啉-2,3'[3H]萘并[2,1-b][1,4]噁嗪,对其进行了紫外和红外光谱以及元素分析,并对其光致变色性质以及主要影响因素温度、溶剂和pH进行了研究.结果表明,该化合物具有良好的光致变色性和一定的酸致变色性;温度、溶剂极性和pH对其光致变色性有不同程度的影响.     

吲哚啉苯并螺呲喃类化合物的合成和应用

吲(口朶)啉苯并螺吡喃类化合物具有明显的光致变色性能。我们合成了6′-碘-1,3,3-三甲基吲(口朶)啉-2-螺环-2′-苯并吡喃及一些不同取代的吲(口朶)啉苯并螺吡喃化合物并对其色变性能进行了初步探讨。用这些化合物与光致抗蚀干膜G11胶制成了一种新型光致变色抗蚀干膜。将底片覆盖在此膜上,经紫外线照射后呈现出明显的色差,显示出的图象可保留24小时以上。     

Synthesis and properties of photochromic cholesteric liquid crystalline polysiloxane containing chiral mesogens and azobenzene photochromic groups

A series of novel thermotropic side‐chain liquid crystalline polymers(P₀–P₁₂) were synthesized by grafting copolymerization of mesogenic monomer cholesteryl undecylenate (M1) and photochromic monomer 4‐allyoxy‐4′‐nitroazobenzene (M2) on polymethylhydrosiloxane. The chemical structures of polymers were characterized by infrared (IR) and ultraviolet (UV) spectroscopy. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) were used to measure the thermal properties of those polymers, and the mesogenic properties were characterized by polarized optical micrograph, DSC, wide‐angle X‐ray diffraction and small‐angle X‐ray scattering. The glass transition temperatures (T_gs) of the polymers increased from P₀ to P₄ and decreased from P₅ to P₁₂. The clearing point temperatures (T_is) of the polymers P₁–P₁₂ were lower than that of P₀, but increased from P₁ to P₄ and decreased from P₅ to P₁₂. They showed thermotropic liquid crystalline properties in a broad mesogenic region at temperatures >100°C. The polymers P₀–P₈ exhibited a cholesteric mesophase with oily streaks and lined texture, and polymers P₉–P₁₂ showed a chiral smectic mesogenic phase with a layered texture. All of the polymers were thermally stable to ～ 320°C. The UV‐induced trans–cis photoisomerization was investigated for the azo monomer and polymers P₈ and P₁₂. The solution of the azo monomer and liquid crystalline polymers P₈ and P₁₂ can undergo photoisomerization, and the environments of the azo group were responsible for the aforementioned photochemical process. © 2002 Wiley Periodicals, Inc. J Appl Polym Sci 85: 2155–2162, 2002     

有机光致变色夹胶玻璃

首先制备了螺旋吡喃类有机光致变色粉,并用该变色粉合成了PVB光致变色胶片和有机光致变色夹胶玻璃样品。测量了该有机光致变色夹胶玻璃样品在光照3min前后的可见光透光率变化情况,并推算其遮阳系数及隔热效果等。     

Industrial organic photochromic dyes

Organic photochromic molecules are well established as colorants in the manufacture of niche products, providing striking colour change effects when irradiated with light. This paper describes the industrially important classes of photochromic dye in terms of their development and chemistries, the applications in which their photochromism is employed commercially, and the technical features behind their success. Photochromic systems form the subject of much industrially funded research into nascent high‐tech applications that have the potential to become the most commercially significant outlets for photochromic dyes. Those types being scrutinised are therefore also discussed along with the directions in which the industrial use of photochromic colorants may take.     

Langmuir-Blodgett-films of photochromic polyglutamates

Summary Polyglutamates bearing azobenzene derivatives covalently bound to the main chain via spacers and equipped with alkyl tails of different length have been synthesized. In the polymers the chromophore can be isomerized to high extent by irradiation with UV-light. The polymers can be spread on a LANGMUIR trough. The spreading behaviour is different for irradiated and non irradiated samples, indicating a different arrangement depending on the content of cis-isomer. The films are less stable for longer spacers and smaller tails, caused by the better interaction of the azobenzene groups due to the greater mobility and minor hindrance.Part I: see [8]     

Properties of photochromic retinals

In the present review, we summarize our recent studies on the synthesis and spectral-kinetic parameters of photochromic retinals based on spiropyrans, diarylethenes, and a fulgimide and the use of these compounds for the preparation of artificial analogs of natural bacteriorhodopsin.     

一种光致变色水凝胶的合成与表征

合成了一种结合了螺吡喃(SP)的光致变色水凝胶,即N-乙烯基吡咯烷酮与N-异丙基丙烯酰胺共聚物水凝胶.红外光谱和溶胀实验的结果都表明,螺吡喃很好地结合进了水凝胶里.紫外-可见光谱的结果证明,合成的水凝胶具有光致变色特性,水凝胶对周期性交替的紫外光照射和黑暗条件的响应情况可以说明其光致变色的可回复性.从荧光显微镜照片可以...     

Exploring the pharmacology and action spectra of photochromic open-channel blockers

Light control of voltage-gated ion channels: We have developed red-shifted derivatives of QAQ, a powerful doubly charged photochromic blocker. These derivatives allow for remote control of K(v) and Na(v) channel conductance with light and offer the opportunity to silence neuronal activity reversibly.     

Synthesis and photochromic properties of a dithiazolylindole

A novel photochromic 2,3-dithiazolylindole has been synthesized and its photochromic properties was elucidated. This compound showed reversible photochromism both in solution and in a crystal with no spontaneous bleaching under dark conditions. The photocyclization quantum yield of the dithiazolylindole was as high as 83% in hexane, suggesting the photoreactive conformation was stabilized through intramolecular interactions. X-ray crystal structure analysis revealed that the dithiazolylindole adopted the photoreactive conformation with quasi-C₂ symmetry around the hexatriene moiety in the crystalline state. This conformation was assisted by presumed intramolecular CH/N hydrogen bonding between the central N-methylindole and the side-chain thiazolyl units in combination with steric interactions between methyl groups at the reactive center carbons. The suggestion of intramolecular hydrogen bonding in solution was also supported by a ¹H NMR variable temperature study.     

Synthesis and photochromic properties of novel spirooxazine

Summary Novel 1-[-(4-trifluromethyl benzoyloxy)ethyl]-3, 3-dimethyl-spiro[indoline-2, 3-[3H]-naphtho[2,1-b]-1,4-oxazine](III) was prepared and their photochromic properties were investigated in polystyrene (PS) films. It is shown that the kinetics of thermal decoloration was decreased with increasing concentration of III in PS films.