bis(4-di-n-butylamino-2-hydroxyphenyl)squaraine | 87286-91-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis(4-di-n-butylamino-2-hydroxyphenyl)squaraine
• 英文别名: bis(4-dibutylamino-2-hydroxyphenyl)squaraine；squaraine
• CAS: 87286-91-7
• 化学式: C₃₂H₄₄N₂O₄
• 分子量: 520.712
• InChiKey: AUVGMLDTWPEAMJ-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  38.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  bis(4-di-n-butylamino-2-hydroxyphenyl)squaraine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2,4-bis<4-(dibutylamino)-2-hydroxyphenyl>-squaraine
  参考文献：
  名称：

  Facile preparative redox chemistry of bis(4-dialkylaminophenyl)squaraine dyes

  摘要：

  Bis(4-dialkylaminophenyl)squaraine dyes are readily reduced in solution by borohydride to give alkali soluble leuco compounds, which exist in the 3-hydroxy-2,4-(4-dialkylaminophenyl)cyclobutenone tautomeric form. The leuco dyes can be oxidised rapidly back to the squaraine dye, thus providing a means of temporarily solubilising the squaraine dye in water. The leuco compounds undergo Substitution reactions typical of vinylogous carboxylic acids. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01857-9
• 作为产物：
  描述：

  3-氨基苯酚 在 sodium hydroxide 作用下， 以 甲苯 、 正丁醇 为溶剂， 反应 4.5h， 生成 bis(4-di-n-butylamino-2-hydroxyphenyl)squaraine
  参考文献：
  名称：

  Kazmaier, Peter M.; Hamer, Gordon K.; Burt, Richard A., Canadian Journal of Chemistry, 1990, vol. 68, # 4, p. 530 - 536

  摘要：

  DOI：

文献信息

• HIGH PERFORMANCE LUMINESCENT COMPOUNDS
  申请人：Smith Bradley

  公开号：US20110118459A1

  公开（公告）日：2011-05-19

  Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to novel near-infrared dyes that are photostable and resistant to quenching. The dyes belong to a novel family of squaraine rotaxanes, and they are particularly well-suited for use in biological applications. Also disclosed are methods of synthesizing the dyes and methods of using the dyes.

  该实施例涉及化学和生物化学领域，更具体地涉及新型近红外染料，这些染料具有光稳定性并且抗猝灭。这些染料属于一种新型的方酮轮烷家族，特别适用于生物应用。还公开了合成这些染料的方法和使用这些染料的方法。
• [EN] HIGH PERFORMANCE LUMINESCENT COMPOUNDS<br/>[FR] COMPOSÉS LUMINESCENTS HAUTE PERFORMANCE
  申请人：UNIV NOTRE DAME DU LAC

  公开号：WO2011059457A1

  公开（公告）日：2011-05-19

  Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to novel near-infrared dyes that are photostable and resistant to quenching. The dyes belong to a novel family of squaraine rotaxanes, and they are particularly well-suited for use in biological applications. Also disclosed are methods of synthesizing the dyes and methods of using the dyes.

  该实施例涉及化学和生物化学领域，更具体地涉及新型近红外染料，这些染料具有光稳定性并且抗猝灭。这些染料属于一种新型的方酮轮烷家族，它们特别适用于生物应用。还公开了合成这些染料的方法和使用这些染料的方法。
• 착색 경화성 수지 조성물
  申请人：DONGWOO FINE-CHEM CO., LTD. 동우 화인켐 주식회사(119990493297) Corp. No ▼ 214911-0005738BRN ▼125-85-13136

  公开号：KR20150034626A

  公开（公告）日：2015-04-03

  본 발명은, C.I. 피그먼트 옐로우 138, 녹색 안료 및 황색 염료로 이루어진 군에서 선택되는 적어도 1종의 착색제(A1)와, 스쿠아릴리움 염료(A2)와, 수지(B)와, 중합성 화합물(C)과, 중합 개시제(D)와, 용제(E) 를 포함하는 착색 경화성 수지 조성물을 제공하는 것을 목적으로 한다.

  本发明旨在提供一种包括选择自C.I.颜料黄138、绿色颜料和黄色染料组成的一组中至少一种着色剂(A1)、Squarilium染料(A2)、树脂(B)、聚合物(C)、聚合起始剂(D)和溶剂(E)的着色固化树脂组合物。
• A New Class of Hydroxy-Substituted Squaraine Rotaxane
  作者：Na Fu、Jeremiah J. Gassensmith、Bradley D. Smith

  DOI：10.1071/ch09671

  日期：——

  A templated macrocyclization reaction was used to permanently encapsulate a highly fluorescent hydroxy-substituted squaraine dye inside a tetralactam macrocycle. The free squaraine dye is quite rigid due to internal hydrogen bonding and its photophysical properties hardly change upon encapsulation. A combination of X-ray and NMR data show that the surrounding tetralactam macrocycle adopts an unusually rigid chair conformation and does not undergo rapid pirouetting. Because of its large size and conformational rigidity, the macrocycle creates anisotropic NMR shielding zones that extend over the N,N-dibutylamino groups at each end of the squaraine thread. This shielding anisotropy allows hindered aryl-N rotation to be observed by NMR spectroscopy and provides direct experimental evidence that quinoid-like resonance structures are major contributors to the bis(N,N-dialkylaminophenyl)squaraine resonance hybrid.

  通过模板化大环化反应，将一种高荧光羟基取代的角鲨烷染料永久封装在四内酰胺大环内。由于内部氢键的作用，游离的角鲨烷染料非常坚硬，其光物理性质在封装后几乎没有变化。结合 X 射线和核磁共振数据可以看出，周围的四内酰胺大环采用了异常坚硬的椅子构象，不会发生快速回旋。由于其尺寸大、构象刚性强，大环在方碱线两端的 N,N-二丁氨基基团上形成了各向异性的核磁共振屏蔽区。这种屏蔽各向异性使得 NMR 光谱能够观察到受阻的芳基-N 旋转，并提供了直接的实验证据，证明类醌共振结构是双（N,N-二烷基氨基苯基）角鲨烷共振混合体的主要成分。
• New Two-Photon Absorbing Squaraine Derivative with Efficient Near-Infrared Fluorescence, Superluminescence, and High Photostability
  作者：Mykhailo V. Bondar、Sanaz Faryadras、Natalia Munera、Hao-Jung Chang、Mehrun Uddin、Kevin D. Belfield、Olexiy D. Kachkovsky、Eric W. Van Stryland、David J. Hagan

  DOI：10.1021/acs.jpcb.2c01288

  日期：2022.6.2

  photophysical and nonlinear optical properties of a new squaraine derivative 2,4-bis[4-(azetidyl)-2-hydroxyphenyl]squaraine (1) with efficient near-infrared (NIR) emission was comprehensively analyzed based on spectroscopic, photochemical, and two-photon absorption (2PA) measurements, along with quantum chemical analysis. The steady-state absorption, fluorescence, and excitation anisotropy spectra of 1

  综合分析了具有高效近红外（NIR）发射的新型方酸衍生物2,4-双[4-（氮杂环丁烷基）-2-羟基苯基]方酸（1）的线性光物理性质和非线性光学性质，基于光谱，光化学和双光子吸收 (2PA) 测量，以及量子化学分析。1的稳态吸收、荧光和激发各向异性光谱及其荧光发射寿命揭示了 1 电子结构的多个方面，包括主要跃迁偶极子的相对取向、不同极性溶剂中的有效旋转体积以及最大摩尔消光度为 1.35 × 10 –5 M –1 ·cm–1，对于类似的对称方晶，它异常小。使用标准开孔 Z 扫描和双光子诱导荧光方法，在飞秒激发下的宽光谱范围内获得1的简并 2PA 光谱，显示最大 2PA 横截面约为 400 GM。在飞秒泵浦条件下， Squaraine 1在室温下在极性溶剂（二氯甲烷）中表现出高效的超发光发射。使用 DFT/TD-DFT 理论水平对1的电子结构进行量子化学分析，发现与实验数据非常吻合。新方酸衍生物1