2-[(E)-2-(2-Hydroxy-5-nitro-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium | 90281-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(E)-2-(2-Hydroxy-5-nitro-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium
• 英文别名: 4-nitro-2-[(Z)-2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]phenol
• CAS: 90281-24-6
• 化学式: C₁₉H₁₉N₂O₃
• 分子量: 323.371
• InChiKey: IENILPMDTHYRMT-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(E)-2-(2-Hydroxy-5-nitro-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium 在 丙二酸 作用下， 以 水 为溶剂， 生成 螺[1,3,3-三甲基吲哚-(6'-硝基苯并二氢吡喃)]
  参考文献：
  名称：

  Time-Resolved Thermodynamic Profile upon Photoexcitation of a Nitrospiropyran in Cycloalkanes and of the Corresponding Merocyanine in Aqueous Solutions

  摘要：

  The photoconversion of 2',3'-dihydro-6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indole] (Sp) to its open merocyanine form (Me) in a series of aerated cycloalkanes (cyclopentane, cyclohexane, and trans- and cis-decalin) and of the protonated merocyanine (McH(+)) to Sp in aqueous solution were studied by laser-induced optoacoustic spectroscopy (LIOAS). The + (11 +/- 2) ml mol(-1) expansion determined for the ring closure is due to deprotonation of McH(+) plus the reaction of the ejected proton with the monoanion of malonic acid (added to stabilize Mc), an intrinsic expansion and a small electrostriction term. The energy difference between Sp and initial McH(+) is (282 +/- 110) kJ mol(-1). An intrinsic contraction of - (47 +/- 15) ml mol(-1) occurs upon ring opening, forming triplet (3)Mc in the cycloalkanes, whereas no volume change was detected for the (3)Mc to Mc relaxation. Electrostriction decreases the (3)Mc energy, (165 +/- 18) kJ mol(-1), to 135 kJ mol(-1). The difference in the values of the ring-opening (Sp to Me) reaction enthalpy in cycloalkanes as derived from the temperature dependence of the Sp reversible arrow Me equilibrium, (29 +/- 8) kJ mol(-1), and from the LIOAS data, - (9 +/- 25) kJ mol(-1), is due to the formation of Mc-Sp aggregates during steady-state measurements. The Sp-sensitized singlet molecular oxygen, O-2((1)Delta (g)), was taken as a, quantum yield (average Phi (Delta) = 0.58 +/- 0.03) derived from the near-IR emission of O-2((1)Delta (g)), measure of Me production in the cycloalkanes, These solvents, albeit troublesome in their handling, provide an additional series for the determination of structural volume changes in nonaqueous media. besides the alkanes already used.

  DOI：

  10.1002/1522-2675(20010919)84:9<2557::aid-hlca2557>3.0.co;2-u
• 作为产物：
  描述：

  merocyanine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 生成 2-[(E)-2-(2-Hydroxy-5-nitro-phenyl)-vinyl]-1,3,3-trimethyl-3H-indolium
  参考文献：
  名称：

  Switchable polarity solvent (SPS) systems: probing solvatoswitching with a spiropyran (SP)–merocyanine (MC) photoswitch

  摘要：

  1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）和醇（如1-丙醇）的可切换极性溶剂（SPS）在CO2的作用下可逆地切换为更高极性的离子液体[DBUH+][RCO3→]。在研究SPS用于控制螺吡喃（SP）-MC分子光开关中亚甲基蓝（MC）形式的寿命时，发现了一种具有独特性质的长寿命物质。在DBU存在的情况下，SP在1-丙醇（PrOH）中的照射会产生一种新物质（最大吸收峰=420 nm）。当CO2产生[DBUH+][PrOCOO→]时，该物质会转化为MC。据推测，1,2和1,4烷氧基加成产物的混合物是由于对MC的共轭二烯系统的亲核攻击而形成的，其中烷氧基的形成是由于高碱性DBU和醇的平衡作用而产生的。这些加合物在CO2或酸的添加下会恢复为MC。通过贝内西-希尔德布兰德分析法，可以确定涉及DBU的烷氧基加成形成的总平衡常数。

  DOI：

  10.1039/c3ob41204k

文献信息

• Reimageable paper
  申请人：Iftime Gabriel

  公开号：US20070054215A1

  公开（公告）日：2007-03-08

  An image forming medium includes a substrate and an imaging layer including a photochromic material and a polymer binder coated on the substrate, where the photochromic material exhibits a reversible homogeneous-heterogeneous transition between a colorless state and a colored state in the polymer binder.
• SOLVENT-LESS PROCESS FOR PRODUCING TRANSIENT DOCUMENTS
  申请人：IFTIME GABRIEL

  公开号：US20080044747A1

  公开（公告）日：2008-02-21

  An image forming method including (a) providing a reimageable medium comprised of a substrate and a photochromic material, wherein the medium is capable of exhibiting a color contrast and an absence of the color contrast; (b) exposing the medium to an imaging light corresponding to a predetermined image to result in an exposed region and a non-exposed region, wherein the color contrast is present between the exposed region and the non-exposed region to allow a temporary image corresponding to the predetermined image to be visible for a visible time; (c) subjecting the temporary image to an indoor ambient condition for an image erasing time to change the color contrast to the absence of the color contrast to erase the temporary image without using an image erasure device; and (d) optionally repeating procedures (b) and (c) a number of times to result in the medium undergoing a number of additional cycles of temporary image formation and temporary image erasure, wherein the reimageable medium is prepared by a solvent-less process comprising i) heating and melting a photochromic material and a polymer to form a coating composition, and ii) coating the coating composition onto at least one side of a transient document substrate.
• INK COMPOSITION
  申请人：Domino UK Limited

  公开号：US20170260412A1

  公开（公告）日：2017-09-14

  The present invention relates to an inkjet ink comprising a photo-chromic colorant and a UV absorber. The ink may be used as a time-temperature indicator and is particularly useful in packaging food and/or drink to provide an indication of the quality of the contents.
• US7229740B2
  申请人：——

  公开号：US7229740B2

  公开（公告）日：2007-06-12
• US7709164B2
  申请人：——

  公开号：US7709164B2

  公开（公告）日：2010-05-04