3,5-[(2,2-dimethyl)trimethylen]-1,7-di(phenylamino)-1,3,5-heptatrien hydrochloride | 68339-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-[(2,2-dimethyl)trimethylen]-1,7-di(phenylamino)-1,3,5-heptatrien hydrochloride
• 英文别名: N-{2-[3-(2-anilino-vinyl)-5,5-dimethyl-cyclohex-2-enylidene]-ethylidene}-aniline; hydrochloride；N-[2-[5,5-dimethyl-3-(2-phenyliminoethylidene)cyclohexen-1-yl]ethenyl]aniline;hydrochloride
• CAS: 68339-59-3
• 化学式: C₂₄H₂₆N₂*ClH
• 分子量: 378.945
• InChiKey: GHPQLRRAMOZGOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  24.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙基-2-甲基苯并噻唑碘化物 、 3,5-[(2,2-dimethyl)trimethylen]-1,7-di(phenylamino)-1,3,5-heptatrien hydrochloride 生成 3-ethyl-2-(3-{3-[3-(3-ethyl-3H-benzothiazol-2-ylidene)-propenyl]-5,5-dimethyl-cyclohex-2-enylidene}-propenyl)-benzothiazolium; iodide
  参考文献：
  名称：

  Slominskii,Yu.L. et al., Soviet progress in chemistry, 1978, vol. 44, # 8, p. 56 - 57

  摘要：

  DOI：

文献信息

• Polymethine‐Based Semiconducting Polymer Dots with Narrow‐Band Emission and Absorption/Emission Maxima at NIR‐II for Bioimaging
  作者：Ming‐Ho Liu、Zhe Zhang、Yu‐Chi Yang、Yang‐Hsiang Chan

  DOI：10.1002/anie.202011914

  日期：2021.1.11

  Deep‐penetration fluorescence imaging in the second near‐infrared (NIR‐II) window heralds a new era of clinical surgery, in which high‐resolution vascular/lymphatic anatomy and detailed cancerous tissues can be visualized in real time. Described here is a series of polymethine‐based semiconducting polymers with intrinsic emission maxima in the NIR‐IIa (1300–1400 nm) window and absorption maxima ranging

  在第二近红外（NIR-II）窗口中进行的深层渗透荧光成像预示了临床手术的新时代，其中可以实时可视化高分辨率的血管/淋巴管解剖结构和详细的癌组织。这里描述的是一系列基于聚次甲基的半导体聚合物，其固有发射最大值在NIR-IIa（1300–1400 nm）窗口内，吸收最大值在1082至1290 nm之间。这些聚合物在水溶液中以半导体聚合物点（Pdots）的形式制备，其荧光量子产率为0.05–0.18％，它们在活体小鼠的无创性全颅脑成像中具有广阔的空间分辨率和信噪比，具有广阔的应用前景。背景对比。这项研究为将来设计发射NIR-IIa甚至NIR-IIb的Pdot提供了平台。
• Design, Synthesis, and Spectral Luminescent Properties of a Novel Polycarbocyanine Series Based on the 2,2-Difluoro-1,3,2-dioxaborine Nucleus
  作者：Konstantin Zyabrev、Andrey Doroshenko、Elena Mikitenko、Yurii Slominskii、Alexei Tolmachev

  DOI：10.1002/ejoc.200701012

  日期：2008.3

  spectroscopic data point to the polymethinic type of electron-density distribution in the 2,2-difluoro-1,3,2-dioxaborine polymethine dye molecules. The fundamental options for controlling the spectral properties of these dyes by modification of their polymethine chains have been evaluated. One of the new compounds synthesized is remarkable among the known open-chain polymethine dyes for its record high

  已经研究了衍生自 2,2-二氟-1,3,2-二氧杂硼烷的对称聚次甲基染料中生色团的性质。从头算量子化学计算表明，二恶硼啉末端残基的存在稳定了相应聚甲川染料的前沿水平，并使螯合环中氧原子上的电子密度分布比具有无硼无环末端的类似染料结构中的电子密度分布更均匀组。已经从迄今为止未知的嘧啶基退火二氧杂环戊烷合成了一系列新型对称聚碳菁和具有各种桥接聚次甲基发色团的三碳菁系列。吸收、荧光和 13C NMR 光谱数据表明 2,2-二氟-1,3,2-二氧杂硼烷多甲川染料分子中的电子密度分布为多甲型。已经评估了通过修饰它们的聚次甲基链来控制这些染料的光谱特性的基本选项。合成的一种新化合物在已知的开链聚次甲基染料中因其创纪录的高荧光量子产率而引人注目。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Novel benzothiazine dyes for imaging elements
  申请人：Eastman Kodak Company

  公开号：US20030192138A1

  公开（公告）日：2003-10-16

  This relates to a dye represented by Formulae II and IIA below: 1 wherein; R 1 represents a hydrogen, an aryl group containing 6 to 14 carbon atoms, or an alkyl group containing 1 to 12 carbon atoms; R 2 and R 3 together form an aromatic, carbocyclic or heterocyclic ring system containing 6 to 14 atoms; X represents a sulfoxide (S═O), sulfone (SO 2 ), or dicyanovinyl (C(CN) 2 ) group; Y represents a sulfoxide (S═O), sulfone (SO 2 ), carbonyl (C═O) or dicyanovinyl (C(CN) 2 ) group; L 1 , L 2 , and L 3 represent methine groups, wherein the methine groups may combine to form a 5- or 6-membered ring when m is equal to or >1; m is 0, 1, 2, or 3; W is an aryl group; and D is a moiety in conjugation with the X and Y groups.

  这与以下式II和IIA所代表的染料有关：1其中，R1代表氢、含有6到14个碳原子的芳基基团或含有1到12个碳原子的烷基基团；R2和R3一起形成含有6到14个原子的芳香族、环烷或杂环环系；X代表亚砜（S═O）、磺酰基（SO2）或二氰乙烯基（C(CN)2）基团；Y代表亚砜（S═O）、磺酰基（SO2）、羰基（C═O）或二氰乙烯基（C(CN)2）基团；L1、L2和L3代表亚甲基基团，其中亚甲基基团可以结合形成5-或6-成员环，当m等于或大于1时；m为0、1、2或3；W为芳基基团；D是与X和Y基团共轭的基团。
• ?-Pyrylotetracarbocyanines
  作者：M. A. Kudinova、Yu. L. Slominskii、A. I. Tolmachev

  DOI：10.1007/bf00515369

  日期：1983.11
• Efficient Two-Photon Absorbing Acceptor-π-Acceptor Polymethine Dyes
  作者：Lazaro A. Padilha、Scott Webster、Olga V. Przhonska、Honghua Hu、Davorin Peceli、Trenton R. Ensley、Mykhailo V. Bondar、Andriy O. Gerasov、Yuriy P. Kovtun、Mykola P. Shandura、Alexey D. Kachkovski、David J. Hagan、Eric W. Van Stryland

  DOI：10.1021/jp100963e

  日期：2010.6.17

  We present an experimental and theoretical investigation of the linear and nonlinear optical properties of a series of acceptor-pi-acceptor symmetrical anionic polymethine dyes with diethylamino-coumarin-dioxaborine terminal groups and different conjugation lengths. Two-photon absorption (2PA) cross sections (delta(2PA)) are enhanced with an increase of pi-conjugation length in the investigated series of dyes. 2PA spectra for all dyes consist of two well-separated bands. The first band, located within the telecommunications window, occurs upon two-photon excitation into the vibrational levels of the main S-0 -> S-1 transition, reaching a large delta(2PA) = 2200 GM (1 GM = 1 x 10(-50) cm(4) s/photon) at 1600 nm for the longest conjugated dye. The position of the second, and strongest, 2PA band for all anionic molecules corresponds to the second-excited final state, which is confirmed by quantum-chemical calculations and excitation anisotropy measurements. Large delta(2PA) values up to 17 000 GM at 1100 nm are explained by the combination of the large ground- and excited-state transition dipole moments. The three shortest dyes show good photochemical stability and surprisingly large fluorescence quantum yields of approximate to 0.90, approximate to 0.66, and approximate to 0.18 at the red to near-IR region of approximate to 640, approximate to 730, and approximate to 840 nm, respectively. The excited-state absorption spectra for all samples are also studied and exhibit intense bands throughout the visible wavelength region with peak cross section close to 5 x 10(-16) cm(2) with a corresponding red shift with increasing conjugation lengths.