9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydroxanthylium perchlorate

• 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: 9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydroxanthylium perchlorate
• 英文别名: 6-(N,N-diethylamino)-9-(2-carboxyphenyl)-1,2,3,4-tetrahydroxanthylium perchlorate；9-(2'-carboxyphenyl)-6-(N,N-diethylamino)-1,2,3,4-tetrahydroxanthylium perchlorate；[9-(2-carboxyphenyl)-5,6,7,8-tetrahydroxanthen-3-ylidene]-diethylazanium;perchlorate
• 化学式: C₂₄H₂₆NO₃*ClO₄
• 分子量: 475.926
• InChiKey: IQFKRQYUMJGSMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydroxanthylium perchlorate 在 乙酸酐 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 1-(6'-(diethylamino)-3-oxo-4'-(2-(1,3,3-trimethylindolin-2-ylidene)ethylidene)-1',2',3',4'-tetrahydrospiro[isoindoline-1,9'-xanthen]-2-yl)thiourea
  参考文献：
  名称：

  A Unique Class of Near-Infrared Functional Fluorescent Dyes with Carboxylic-Acid-Modulated Fluorescence ON/OFF Switching: Rational Design, Synthesis, Optical Properties, Theoretical Calculations, and Applications for Fluorescence Imaging in Living Animals

  摘要：

  Fluorescence imaging is one of the most powerful techniques for monitoring biomolecules in living systems. Fluorescent sensors with absorption and emission in the near-infrared (NIR) region are favorable for biological imaging . applications in living animals, as NIR light leads to minimum photodamage, deep tissue penetration, and minimum background autofluorescence interference. Herein, we have introduced a new strategy to design NIR functional dyes with the carboxylic-acid-controlled fluorescence on off switching mechanism by the spirocyclization. Based on the design strategy, we have developed a series of Changsha (CS1-6) NIR fluorophores, a unique new class of NIR functional fluorescent dyes, bearing excellent photophysical properties including large absorption extinction coefficients, high fluorescence quantum yields, high brightness, good photostability, and sufficient chemical stability. Significantly, the new CS1-6 NIR dyes are superior to the traditional rhodamine dyes with both absorption and emission in the NIR region while retaining the rhodamine-like fluorescence ON-OFF switching mechanism. In addition, we have performed quantum chemical calculations with the B3LYP exchange functional employing 6-31G* basis sets to shed light on the structure-optical properties of the new CS1-6 NIR dyes. Furthermore, using CS2 as a platform, we further constructed the novel NIR fluorescent TURN-ON sensor 7, which is capable of imaging endogenously produced HCIO in the living animals, demonstrating the value of our new CS NIR functional fluorescent dyes. We expect that the design strategy may be extended for development of a wide variety of NIR functional dyes with a suitable fluorescence-controlled mechanism for many useful applications in biological studies.

  DOI：

  10.1021/ja209292b
• 作为产物：
  描述：

  3-羟基-N,N-二乙基苯胺 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 19.5h， 生成 9-(2-carboxyphenyl)-6-(diethylamino)-1,2,3,4-tetrahydroxanthylium perchlorate
  参考文献：
  名称：

  一种新型的SO 2比色荧光探针及其在活细胞成像中的应用。

  摘要：

  一种新型的基于氧化铬的荧光探针被用于检测二氧化硫（SO 2）。基于对105nm储能位移的碳-碳双键的亲核加成反应，该探针对SO 2表现出了显着的荧光开启响应。该探针已成功应用于SO 2的定量分析。线性检测范围为0-160μM，检测限低至99.27 nM。与其他反应物种和氨基酸相比，它对SO 2的选择性也高。此外，细胞染色实验表明该探针可穿透细胞膜，可用于活细胞中SO 2的高性能成像。探针的优越性能使其在化学和生物学应用中具有广阔的前景。

  DOI：

  10.3390/molecules23040871

文献信息

• Near-infrared fluorescent probe for selective detection of Cu2+ in living cells and in Vivo
  作者：Zhiyang Xu、Hong Wang、Zhen Chen、Hongli Jiang、Yanqing Ge

  DOI：10.1016/j.saa.2019.03.062

  日期：2019.6

  NIR-rhodamine fluorescent probe was designed and successfully synthesized. The structure of the probe NRh-Cu was characterized by 1H NMR, 13C NMR and HRMS. The probe was found to show high sensitivity and high selectivity. The detection limit was calculated to be as low as 0.95 ppb. The sensing mechanism was proposed and confirmed by HRMS spectra. Furthermore, it could be used for imaging Cu2+ in living cells

  设计并成功合成了NIR-若丹明荧光探针。探针NRh-Cu的结构通过1 H NMR，13 C NMR和HRMS表征。发现该探针显示出高灵敏度和高选择性。计算出的检出限低至0.95 ppb。提出了感应机制，并通过HRMS光谱对其进行了确认。此外，它可用于在活细胞和体内对Cu 2+进行成像。
• 一种不对称近红外菁染料及其制备方法与应 用
  申请人：清华大学

  公开号：CN105585872B

  公开（公告）日：2017-04-19

  本发明公开了一种不对称近红外菁染料及其制备方法与应用。所述不对称近红外菁染料的结构式如式Ⅰ所示。本发明提供的所述不对称近红外菁染料的制备方法，包括如下步骤：(1)式Ⅱ所示化合物与式Ⅲ所示化合物经缩合反应得到式Ⅴ所示化合物；(2)式Ⅴ所示化合物与式Ⅳ所示化合物经缩合反应即得到式Ⅰ所示不对称近红外菁染料。本发明提供的不对称近红外菁染料，其共轭体系大，具有较强的近红外吸收，而荧光量子产率较低，非辐射跃迁的几率较大，因此具较好的光热转化效率；本发明进一步通过生物相容性好的BSA的包裹，既提高了染料的水溶性也延长了体内的保留时间，可作为光热治疗剂用于光热治疗，在肿瘤治疗方面有着非常重要的作用。
• Photochemical behaviour of a new 1,2,3,4-tetrahydroxanthylium fluorescent dye with “rhodamine-like” structure in liquid media and adsorbed onto a TiO2 photo-responsive substrate
  作者：D.S. Conceição、D.P. Ferreira、Y. Prostota、P.F. Santos、L.F. Vieira Ferreira

  DOI：10.1016/j.dyepig.2016.01.030

  日期：2016.5

  Additionally, the behaviour of the dye adsorbed onto TiO2 revealed some interesting features regarding the formation of the radical derived from the dye cation, following the electron injection in the conduction band of the semiconductor. Laser flash photolysis and ground state diffuse reflectance were used to evaluate and discriminate the mechanism of photoexcitation presented, as well as to characterize

  合成了一种基于9-（2'-羧苯基）-6-（N，N-二乙氨基）-1,2,3,4-四氢黄thy系的新型“若丹明”荧光NIR染料。研究了其在溶液中和吸附在TiO 2光敏固体基质上的光谱发光特性。关于液体样品，在二氯甲烷中获得最高的荧光量子产率和荧光寿命（ø ˚F  = 0.28，τ ˚F  = 2.67纳秒），而在乙醇和乙腈，我们观察到最大的斯托克斯位移，表示一个扭曲的分子内电荷转移机构。此外，染料吸附到TiO 2上的行为揭示了一些有趣的特征，这些特征涉及在电子注入到半导体的导带中之后，染料阳离子衍生的自由基的形成。激光闪光光解法和基态漫反射率用于评估和区分所提出的光激发机理，以及表征分子的光稳定性。在这种情况下，可以识别两种不同的情况：自光敏途径和光催化机理。
• A new chromenylium-cyanine chemosensor for switch-ON near-infrared copper (II) sensing
  作者：Kaan Karaoglu

  DOI：10.1016/j.molstruc.2019.127640

  日期：2020.4

  response to copper ions at the range of 0–4.9 × 10−6 M in the presence of other competing metal ions, such as Na+, K+, Mg2+, Ca2+, Cr3+, Mn2+, Fe3+, Co2+, Ni2+, Zn2+, Al3+, Cd2+, Ag+, Sr2+, Pb2+, Hg2+ and Ba2+. The limit of detection (LOD) was calculated as 1.28 × 10−8 M which was lower than that of previously reported analogues. The sensor allows detection of the copper(II) ion through the spirocyclic

  摘要 设计并合成了一种具有高选择性和灵敏度的近红外化学传感器，其具有用于检测水样中的 Cu2+ 的铬镍鎓-花青骨架。在其他竞争性金属离子（如 Na+、K+、Mg2+、Ca2+、Cr3+、Mn2+、Fe3+、Co2+、Ni2+）存在的情况下，该传感器对 0–4.9 × 10−6 M 范围内的铜离子表现出线性光学响应、Zn2+、Al3+、Cd2+、Ag+、Sr2+、Pb2+、Hg2+ 和 Ba2+。检测限 (LOD) 计算为 1.28 × 10-8 M，低于先前报道的类似物。该传感器允许通过 Cu2+ 配位的螺环开环反应检测铜 (II) 离子。
• 一种类罗丹明化合物及其合成方法和用途
  申请人：济南大学

  公开号：CN108358882B

  公开（公告）日：2021-06-08

  本发明公开了一种类罗丹明化合物及其合成方法和用途，涉及一种类罗丹明衍生物，其结构式如下式所示：本发明所提供的类罗丹明化合物，可对甲醇进行可视化检测，与其他醇类进行肉眼区分；可对甲醇‑乙醇混合液中进行甲醇含量的检测，进而避免工业用乙醇中掺入甲醇超标造成甲醇中毒等。本发明的类罗丹明化合物还可以用于水中乙醇含量的测定，可较简便的测定酒精度。本发明中所采用的合成方法原料易得，操作简单，可实现工业化生产。