[2-(pyren-1-yl)-2,3-dihydro-1H-perimidine]

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: [2-(pyren-1-yl)-2,3-dihydro-1H-perimidine]
• 英文别名: 2‑(pyren‑1‑yl)‑2,3‑dihydro‑1H‑perimidine；2-Pyren-1-yl-2,3-dihydro-1h-perimidine；2-pyren-1-yl-2,3-dihydro-1H-perimidine
• 化学式: C₂₇H₁₈N₂
• 分子量: 370.453
• InChiKey: LYYDLFIKKRBPLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  铜 、 [2-(pyren-1-yl)-2,3-dihydro-1H-perimidine] 以 水 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of a novel pyrene derived perimidine and exploration of its aggregation induced emission, aqueous copper ion sensing, effective antioxidant and BSA interaction properties

  摘要：

  A new pyrene derived dihydroperimidine [2-(pyren-1-yl)-2,3-dihydro-1H-perimidine (1)] was synthesized and characterized by H-1-NMR, C-13-NMR, HRMS spectroscopic techniques. The perimidine 1 was found to be a very interesting AIE luminogen with highest emission at 4:1 water acetonitrile mixture. Compound 1 is a selective naked eye calorimetric sensor for aqueous Cu2+ (colorless sensor turned brownish yellow upon contact with Cu2+ ion) and gives turn off fluorescence responses in excited state spectroscopy with a limit of detection in the nanomolar range. Further it is an effective antioxidant which has been validated via 2,2-diphenyl-1-picrylhy-drazyl assay and cyclic voltammetric studies in comparison to a well-known antioxidant L-ascorbic acid. To say vehemently antioxidant 1 has proven itself 5.9 times better than L-ascorbic acid. The perimidine 1 manifested interaction with protein bovine serum albumin via quenching of its own intrinsic emission intensity in Tris-HCl buffer.

  DOI：

  10.1016/j.jphotochem.2019.03.014
• 作为产物：
  描述：

  1-芘甲醛 、 1,8-二氨基萘 在 biochar sulfonic acid 作用下， 以 乙醇 为溶剂， 以93 %的产率得到[2-(pyren-1-yl)-2,3-dihydro-1H-perimidine]
  参考文献：
  名称：

  释放源自榕树皮的生物炭磺酸的潜力：从合成和表征到其在哌啶绿色合成中惊人催化作用的旅程

  摘要：

  在这项研究中，开发了一种酸改性生物炭催化剂，用于合成哌啶衍生物，利用菩提树的树皮作为生物炭形成的碳源。该催化剂是通过在 550 °C 下热解然后用氯磺酸处理而生产的。通过傅里叶变换红外光谱、X射线衍射、扫描电子显微镜和能量色散X射线光谱对合成的催化剂生物炭磺酸（BCSA）进行了表征。通过 1,8-二氨基萘与各种羰基化合物（酮和醛）的环缩合反应，在短反应时间（< 1 小时）内制备了多种萘嵌间二氮杂苯衍生物，产率很高（72-95%）。 。我们新开发的方案展示了一系列环保属性，包括无金属合成、一锅单步操作、催化剂可回收性、广泛的底物范围以及克级合成的能力。这项工作标志着可持续催化和绿色化学过程的重大进步。

  DOI：

  10.1007/s11164-023-05199-w

文献信息

• Synthesis of a novel pyrene derived perimidine and exploration of its aggregation induced emission, aqueous copper ion sensing, effective antioxidant and BSA interaction properties
  作者：Nilanjan Chakraborty、Senjuti Banik、Arijit Chakraborty、Swapan Kumar Bhattacharya、Suman Das

  DOI：10.1016/j.jphotochem.2019.03.014

  日期：2019.5

  A new pyrene derived dihydroperimidine [2-(pyren-1-yl)-2,3-dihydro-1H-perimidine (1)] was synthesized and characterized by H-1-NMR, C-13-NMR, HRMS spectroscopic techniques. The perimidine 1 was found to be a very interesting AIE luminogen with highest emission at 4:1 water acetonitrile mixture. Compound 1 is a selective naked eye calorimetric sensor for aqueous Cu2+ (colorless sensor turned brownish yellow upon contact with Cu2+ ion) and gives turn off fluorescence responses in excited state spectroscopy with a limit of detection in the nanomolar range. Further it is an effective antioxidant which has been validated via 2,2-diphenyl-1-picrylhy-drazyl assay and cyclic voltammetric studies in comparison to a well-known antioxidant L-ascorbic acid. To say vehemently antioxidant 1 has proven itself 5.9 times better than L-ascorbic acid. The perimidine 1 manifested interaction with protein bovine serum albumin via quenching of its own intrinsic emission intensity in Tris-HCl buffer.
• Unlocking the potential of Ficus religiosa tree bark-derived biochar sulfonic acid: a journey from synthesis and characterization to its astonishing catalytic role in green synthesis of perimidines
  作者：Sunita Teli、Shivani Soni、Pankaj Teli、Nusrat Sahiba、Shikha Agarwal

  DOI：10.1007/s11164-023-05199-w

  日期：2024.3

  In this research, an acid-modified biochar catalyst was developed for the synthesis of perimidine derivatives, utilizing the bark of the Ficus religiosa (peepal) tree as a carbon source for the biochar formation. The catalyst was produced through pyrolysis at 550 °C followed by treatment with chlorosulfonic acid. The synthesized catalyst, biochar sulfonic acid (BCSA) was characterized by fourier-transform

  在这项研究中，开发了一种酸改性生物炭催化剂，用于合成哌啶衍生物，利用菩提树的树皮作为生物炭形成的碳源。该催化剂是通过在 550 °C 下热解然后用氯磺酸处理而生产的。通过傅里叶变换红外光谱、X射线衍射、扫描电子显微镜和能量色散X射线光谱对合成的催化剂生物炭磺酸（BCSA）进行了表征。通过 1,8-二氨基萘与各种羰基化合物（酮和醛）的环缩合反应，在短反应时间（< 1 小时）内制备了多种萘嵌间二氮杂苯衍生物，产率很高（72-95%）。 。我们新开发的方案展示了一系列环保属性，包括无金属合成、一锅单步操作、催化剂可回收性、广泛的底物范围以及克级合成的能力。这项工作标志着可持续催化和绿色化学过程的重大进步。