1',3'-dihydro-1'-(3-carbomethoxypropyl)-3',3'-dimethyl-6-nitrospiro[2H-1-benzopyran-2,2'(2H)-indole] | 285115-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1',3'-dihydro-1'-(3-carbomethoxypropyl)-3',3'-dimethyl-6-nitrospiro[2H-1-benzopyran-2,2'(2H)-indole]
• 英文别名: 1'-(3-carbomethoxypropyl)-3',3'-dimethyl-6-nitrospiro[2H-1]benzopyran-2,2'-indoline；1'-(3-Carbomethoxypropyl)-3,3'-dimethyl-6-nitrospiro[2H-1]benzopyran-2,2'-indoline；Methyl 4-(3',3'-dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)butanoate
• CAS: 285115-57-3
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: ZHACMZRBIPABTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1',3'-dihydro-1'-(3-carbomethoxypropyl)-3',3'-dimethyl-6-nitrospiro[2H-1-benzopyran-2,2'(2H)-indole] 以 various solvent(s) 为溶剂， 生成 Methyl 4-[3,3-dimethyl-2-[2-(3-nitro-6-oxocyclohexa-2,4-dien-1-ylidene)ethylidene]indol-1-yl]butanoate
  参考文献：
  名称：

  All-Photonic Molecular Half-Adder

  摘要：

  One molecule acts as both an AND and an XOR Boolean logic gate that share the same two photonic inputs. The molecule comprises a half-adder, adding two binary digits with only light as inputs and outputs, and consists of three covalently linked photochromic moieties, a spiropyran and two quinolinederived dihydroindolizines. The AND function is based on the absorption properties of the molecule, whereas the XOR function is based on an off-on-off response of the fluorescence to the inputs that results from interchromophore excited-state quenching interactions. The half-adder is simple to operate and can be cycled many times.

  DOI：

  10.1021/ja0654579
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 以 乙醇 、 氯仿 为溶剂， 反应 26.0h， 生成 1',3'-dihydro-1'-(3-carbomethoxypropyl)-3',3'-dimethyl-6-nitrospiro[2H-1-benzopyran-2,2'(2H)-indole]
  参考文献：
  名称：

  Photon-Controlled Phase Partitioning of Spiropyrans

  摘要：

  The reversible partitioning of molecules between immiscible phases, such as in solvent extraction, is usually controlled by chemical composition of one or both phases, temperature, or pH. An additional means for controlling the equilibrium distribution of a solute between phases, the use of light and suitable photochromic molecules, such as those drawn from the spiropyran family, is described. Partitioning of 1',3',3'-trimethyl-6-nitrospiro[2H-1]-benzopyran-2,2' indoline (1'-methyl 6-NO2 BIPS) and its derivatives between toluene and water phases is shown to be controlled by the wavelength of incident light, the ionogenic functional groups on the molecule, and the aqueous solution pH. At pH 2, both 1'-methyl 6-NO2 BIPS and 1'-(3-carbomethoxypropyl) 6-NO2 BIPS partition reversibly and preferentially into the aqueous phase when irradiated with ultraviolet light in the 365-370 nm region but only slightly into the aqueous phase when illuminated with wavelengths greater than or equal to 480 nm. The partition coefficient of these spiropyrans at pH 2 and under irradiation with ultraviolet light is 25 times larger than when irradiated with visible light. For aqueous solutions of 1'-(3-carboxypropyl) 6-NO2 BIPS, the partition coefficient at pH 4 and under UV light irradiation is 22 times larger than that under visible light irradiation, whereas at pH 6 the partition coefficient under UV irradiation is only 2 times greater than under visible light irradiation. These partition coefficient variations are explained by applying chemical equilibrium theory to the reversible, irradiation-induced structural changes in spiropyran molecules. The fit of theory to the data confirms the importance of interface speciation.

  DOI：

  10.1021/jp0003757

文献信息

• Molecular Implementation of Sequential and Reversible Logic Through Photochromic Energy Transfer Switching
  作者：Patricia Remón、Martin Hammarson、Shiming Li、Axel Kahnt、Uwe Pischel、Joakim Andréasson

  DOI：10.1002/chem.201100027

  日期：2011.5.27

  fluorescence switching through modulation of energy transfer. The dyads were designed in such a way that energy transfer is only observed for the open forms of the photochrome (merocyanine and protonated merocyanine), whereas the closed spiropyran is inactive as an energy acceptor. This was made possible through a deliberate choice of fluorophores (4‐amino‐1,8‐naphthalimide, dansyl, and perylene) that produce

  研究了用荧光团修饰的光致变色螺吡喃作为分子平台，通过调节能量转移实现了荧光转换。设计二元组的方式是，仅在开放形式的光致变色剂（硫氰酸和质子化的花菁）中观察到能量转移，而封闭的螺吡喃却没有作为能量受体的活性。通过精心选择的荧光团（4-氨基-1,8-萘二甲酰亚胺，丹磺酰基和per），可以实现与螺环形式的零光谱重叠和对于花菁形式的相当大的重叠，从而使之成为可能。根据福斯特理论，能量传递被认为是高效的，在某些情况下是100％的效率。光子的组合开关（λ光> 530 nm）和化学（基本）输入可创建顺序逻辑设备，这是键盘锁的基本元素。此外，结合基于蒽的酸性变色荧光开关，设计了一种可逆逻辑器件。这样就可以通过多色荧光信号对不同的输入组合进行明确的编码。可以方便地将所有设备重置为其初始状态并重复循环。
• Photoactivated ratiometric copper(<scp>ii</scp>) ion sensing with semiconducting polymer dots
  作者：Pei-Jing Wu、Jia-Lin Chen、Chuan-Pin Chen、Yang-Hsiang Chan

  DOI：10.1039/c2cc37848e

  日期：——

  This paper describes a simple platform that employs spiropyran-functionalized semiconducting polymer dots as a fluorescent probe for photoactivated ratiometric and sensitive Cu2+ detection, in which the sensing mechanism is based on photogenerated merocyanine that can selectively bind Cu2+ to induce Förster resonance energy transfer.

  本文介绍了一种利用螺吡喃官能化半导体聚合物点作为荧光探针的简易平台，用于光激活比率法和灵敏的 Cu2+ 检测，其中的传感机制基于光生梅洛菁，梅洛菁可选择性地结合 Cu2+ 以诱导佛斯特共振能量转移。
• Photo-Swichable Surfaces with Controllable Physico-Chemical Properties
  申请人：Diamond Dermot

  公开号：US20080261323A1

  公开（公告）日：2008-10-23

  Photochromic materials, such as spiropyran dyes, are disclosed that can be used for high-density optical storage and molecular switches. According to the disclosure these compounds can be used as transducers in optical sensors. When the spiropyran dye absorbs UV light it switches to the merocyanine form, and this structure has an active binding site for cations. When cations bind to the site, the resulting colored complex has a new absorption band in the visible spectrum. By shining white or green light on the colored complex, the dye is reverted to the closed spiropyran form, and the cation is released. The disclosure optimizes the immobilization of the spiropyran dye onto a polymer substrate via long chain alkyl groups. These long chain alkyl linkers enable the dye to reversibly form the preferred merocyanine (2):(1) cation sandwich complex.