methyl 6-hydroxy-2-(4-methoxyphenyl)-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate | 169682-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: methyl 6-hydroxy-2-(4-methoxyphenyl)-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate
• 英文别名: Methyl 6-hydroxy-2-(4-methoxyphenyl)-2-phenylbenzo[h]chromene-5-carboxylate
• CAS: 169682-17-1
• 化学式: C₂₈H₂₂O₅
• 分子量: 438.48
• InChiKey: UUGOCFMEOZSILH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-hydroxy-2-(4-methoxyphenyl)-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate 、 2,2-bis(2-bromo-2-methylpropanoyloxymethyl)propanoyl chloride 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以1.4 g的产率得到
  参考文献：
  名称：

  Photochromic Polymer Conjugates: The Importance of Macromolecular Architecture in Controlling Switching Speed within a Polymer Matrix

  摘要：

  Naphthopyran-poly(n-butyl acrylate) conjugates with different geometries were assembled using ATRP. First, within a rigid lens matrix, all investigation of the photochromic behavior of various poly(n-butyl acrylate), p(n-BA), homopolymers showed that midplacement of a single dye moiety, made possible using a Y-branching difunctional photochromic initiator, gave superior fade kinetics per chain length of conjugated polymer compared to end-functionalized homopolymers. Furthermore, having the dye pendant from the chain opposed to directly within the chain was also found to be advantageous. Fading kinetics became faster when chain length was increased, except in the case of linear random copolymers made by copolymerization of n-butyl acrylate with a naphthopyran acrylate. A gradient copolymer made with a nonphotochromic difunctional initiator and a naphthopyran methacrylate displayed Superior kinetics. Films consisting or ABA triblock copolymers, incorporating the photochromic in the middle of a sort p(n-BA) section, gave slower switching speeds compared to lens samples, with responses that were highly tunable and dependent on the amount of soft section inhabited by the photochromic moiety.

  DOI：

  10.1021/ma901830b

文献信息

• Optimizing the photochromic performance of naphthopyrans in a rigid host matrix using poly(dimethylsiloxane) conjugation
  作者：Francesca Ercole、Nino Malic、Thomas P. Davis、Richard A. Evans

  DOI：10.1039/b904345d

  日期：——

  A series of methoxy substituted 2,2-diaryl-2H-naphthopyran photochromic dyes were assembled incorporating hydroxy functionality to allow their subsequent attachment to flexible poly(dimethylsiloxane) oligomers. The photochromic performance of the generated PDMS–naphthopyran conjugates was studied in a thermoset host matrix and compared to non-conjugated, electronically equivalent control dyes. Both coloration and decoloration speeds were found to be greatly improved with critical T1/2 decoloration times reduced by 42–80%. The extent of solution-like performance provided by PDMS conjugation in the rigid host was examined with reference to the fade performance of control dyes in solution, and found to range from 20 to 90%. These measures are believed to be influenced by the electronic nature and steric interactions of the photochromic dyes.

  一系列甲氧基取代的2,2-二芳基-2H-萘并吡喃光致变色染料被合成并通过引入羟基功能性，以便随后将其固定到柔性的聚二甲基硅氧烷低聚物中。研究了生成的PDMS-萘并吡喃共轭物在热固性基质中的光致变色性能，并与非共轭、电子等效的对照染料进行了比较。发现着色和褪色的速度都大幅提高，关键的褪色半衰期T1/2减少了42-80%。PDMS共轭在刚性基质中提供的类似溶液性能的程度，参考了对照染料在溶液中的褪色性能进行了考察，发现范围从20%到90%不等。这些测量结果被认为受到光致变色染料的电子性质和立体相互作用的影响。
• PHOTOCHROMIC POLYDIORGANOSILOXANE VINYLIC CROSSLINKERS
  申请人：Alcon Inc.

  公开号：US20210284806A1

  公开（公告）日：2021-09-16

  The invention provides a class of photochromic polydiorganosiloxane vinylic crosslinkers. Each of the photochromic polydiorganosiloxane vinylic crosslinkers of the invention comprise (1) a polydiorganosiloxane polymer chain comprising dimethylsiloxane units and photochromic siloxane unit having one methyl substituent and one organic substituent having a photochromic moiety that capable of undergoing a reversible color change upon exposure to UV-irradiation or high-energy-violet light; (2) two terminal ethylenically-unsaturated groups. The invention also provides a soft photochromic contact lens, especially a photochromic silicone hydrogel contact lens, which comprises a crosslinked polymeric material comprising repeating units of at least one of such a class of photochromic polydiorganosiloxane vinylic crosslinkers. The invention further provides a method of producing a photochromic contact lens from a polymerizable composition comprising at least one of such a class of photochromic polydiorganosiloxane vinylic crosslinkers.
• METHOD FOR MAKING PHOTOCHROMIC CONTACT LENSES
  申请人：Alcon Inc.

  公开号：US20210371731A1

  公开（公告）日：2021-12-02

  Described herein is a cost-effective and time-efficient method for producing photochromic contact lenses, in particular, preferably photochromic silicone hydrogel contact lenses, from a polymerizable composition comprising an unique selection and combination of main polymerizable components, a photochromic compound and a visible-light photoinitiator, based on the Lightstream Technology™. This invention also provides photochromic contact lenses or more preferably photochromic silicone hydrogel contact lenses made according to a method of the invention. A photochromic contact lens of the invention is capable of undergoing a reversible color change upon exposure to UV-irradiation or high-energy-violet light (HEVL) (with wavelengths from 380 nm to 440 nm).
• METHOD FOR MAKING PHOTOFUNCTIONAL CONTACT LENSES
  申请人：Alcon Inc.

  公开号：US20220281193A1

  公开（公告）日：2022-09-08

  Described herein is a method for producing a contact lens comprising a central zone that has a diameter of about 13 mm or less, is concentric with the central axis of the contact lens, and possesses at least one photo functionality. The method comprises: applying a first polymerizable fluid composition containing at least one photochemically functional compound on a central portion of the molding surface of a female mold half to form a circular layer; partially curing, in situ, the circular layer in the female mold half; dispensing a second polymerizable fluid composition over the partially-cured circular layer on the molding surface of the female mold half; and a step of curing the second polymerizable fluid composition and the partially-cured circular layer immersed therein in the mold cavity formed between the the molding surfaces of the female mold half and a male mold half.
• US5458814A
  申请人：——

  公开号：US5458814A

  公开（公告）日：1995-10-17