5,10-dimesityl-21-selenatripyrrane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5,10-dimesityl-21-selenatripyrrane
• 英文别名: 2-[[5-[1H-pyrrol-2-yl-(2,4,6-trimethylphenyl)methyl]selenophen-2-yl]-(2,4,6-trimethylphenyl)methyl]-1H-pyrrole
• 化学式: C₃₂H₃₄N₂Se
• 分子量: 525.595
• InChiKey: PCGNYPBAAJTUBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  五氟苯甲醛 、 5,10-dimesityl-21-selenatripyrrane 在 air 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 以7.6%的产率得到5,10,20,25-tetramesityl-15,30-dipentafluorophenyl-35,38-diselenahexaphyrin
  参考文献：
  名称：

  26π Aromatic Core-Modified Hexaphyrins:  Syntheses, Characterization, and Structural Diversities

  摘要：

  Synthesis and characterization of several 26 pi core-modified hexaphyrins are reported. The synthetic methodology involved a well-known acid-catalyzed MacDonald-type condensation reaction of the required tripyrrane with electron deficient pentafluorobenzaldehyde. The nature of the product and yield depends on the nature of the acid catalyst and its concentration. Dioxahexaphyrin 9 was isolated only when 0.5 equiv of TFA was used as a catalyst, while dithiahexaphyrin 10 and diselenahexaphyrin 11 were formed with TFA, PTSA, and even in the absence of catalyst. The detailed H-1 and 2-D COSY as well as HSQC experiments reveal the solution structure as well as the conformational mobility of hexaphyrins. In the tetracationic state, 10 and 11 exhibit a four heterocyclic ring inverted structure, while only two completely inverted heterocyclic rings were observed for 9. The other four heterocyclic rings are only partially inverted in 9. All the hexaphyrins reported here show aromatic character inferred from large Delta delta values (difference in chemical shift between the most shielded and the most deshielded protons). Electronic absorption spectral studies also support the conformational changes observed upon protonation.

  DOI：

  10.1021/jo061861e

文献信息

• Core-Modified Expanded Porphyrins with Large Third-Order Nonlinear Optical Response
  作者：Harapriya Rath、Jeyaraman Sankar、Viswanathan PrabhuRaja、Tavarekere K. Chandrashekar、Amit Nag、Debabrata Goswami

  DOI：10.1021/ja0537575

  日期：2005.8.24

  The third-order nonlinear optical response through measurement of two-photon absorption cross-sections (TPACS) for aromatic core-modified expanded porphyrin analogues by a femtosecond open aperture Z-scan method is reported. The values reported here are among the largest known so far in the literature for any organic molecules.

  报道了通过飞秒开孔 Z 扫描方法测量芳香核修饰的膨胀卟啉类似物的双光子吸收截面 (TPACS) 的三阶非线性光学响应。此处报告的值是迄今为止所有有机分子文献中已知的最大值之一。
• One-Pot Synthesis of Core-Modified Rubyrin, Octaphyrin, and Dodecaphyrin: Characterization and Nonlinear Optical Properties
  作者：Rajeev Kumar、Rajneesh Misra、Tavarekere K. Chandrashekar、Amit Nag、Debabrata Goswami、Eringathodi Suresh、Cherumuttathu H. Suresh

  DOI：10.1002/ejoc.200700466

  日期：2007.9

  Modified 26π rubyrin, 36π octaphyrin, and 54π dodecaphyrin systems have been synthesized in moderately good yields through acid-catalyzed condensations of terthiophene diols and tripyrranes. The product distributions are decided both by the acid catalyst concentration and by the nature of the meso substituents. For example, a new isomer of [26]hexaphyrin(1.1.1.1.0.0) (rubyrin) was obtained with 0.3

  通过三噻吩二醇和三吡喃的酸催化缩合，已经以中等良好的收率合成了改性的 26π 红宝石、36π 八卟啉和 54π 十二烷系统。产物分布由酸催化剂浓度和内消旋取代基的性质决定。例如，获得了 0.3 当量的 [26] 六卟啉 (1.1.1.1.0.0)（红宝石）的新异构体。对甲苯磺酸，当至少一种前体中的内消旋取代基是甲基时。对三噻吩二醇中的对甲氧基取代基的甲基取代基的变化导致形成 [3 + 3 + 3 + 3] 缩合产物 - [54] 十二烷醇 (1.1.1.1.0.0.1.1.1.1.0.0) – 除了预期的红宝石。此外，酸浓度增加到 0.6 当量。导致形成新的 [36] 八茶碱 (1.1.1.1.1.1.0.0)，以及红宝石和十二茶碱。Octphyrin 的单晶 X 射线分析代表了具有 6 个内消旋链的 Octphyrin 平面构象的第一个例子。在红宝石 19 中，与三噻吩亚基相对的一个噻吩环被反转，而在八菲林
• Meso Aryl Heptaphyrins:  The First 30π Aromatic Expanded Porphyrins with an Inverted Structure
  作者：Venkataramana Rao. G. Anand、Simi K. Pushpan、Alagar Srinivasan、Seenichamy Jeyaprakash Narayanan、Bashyam Sridevi、Tavarekere K. Chandrashekar、Raja Roy、Bhavani S. Joshi

  DOI：10.1021/ol000251c

  日期：2000.11.1

  [reaction: see text] Synthesis of new meso aryl 30pi heptaphyrins 2, 3, and 4 is achieved. Spectroscopic studies reveal that 2, 3, and 4 are aromatic and possess an inverted structure.

  [反应：见正文]实现了新的内消旋芳基30pi七卟啉2、3和4的合成。光谱研究表明2、3和4是芳族的并且具有倒置的结构。
• First structural characterization of core modified 10,15-meso aryl azuliporphyrins: observation of C–H⋯π interaction between pyrrole β-CH and mesityl ring
  作者：Sundararaman Venkatraman、Venkataramanarao G. Anand、Viswanathan PrabhuRaja、Harapriya Rath、Jeyaraman Sankar、Tavarekere K. Chandrashekar、Weijie Teng、Karin Ruhlandt Senge

  DOI：10.1039/b204642c

  日期：——

  First successful syntheses and structural characterization of new core modified meso aryl azuliporphyrins by a simple [3 + 1] methodology are reported.

  报告首次采用简单的 [3 + 1] 方法成功合成了新的核心修饰介芳基偶氮卟啉，并对其结构进行了表征。
• Core-Modified<i>meso</i>-Aryl Hexaphyrins with an Internal Thiophene Bridge: Structure, Aromaticity, and Photodynamics
  作者：Ganesan Karthik、Mahima Sneha、V. Prabhu Raja、Jong Min Lim、Dongho Kim、A. Srinivasan、Tavarekere K. Chandrashekar

  DOI：10.1002/chem.201203737

  日期：2013.2.4

  synthesis of core‐modified meso aryl hexaphyrins with an internal thiophene bridge is reported. Introduction of the thiophene bridge alters the electronic structure as well as the π‐electron circuit, resulting in increases in singlet lifetime (τs) and the two‐photon absorption (TPA) cross‐section. Furthermore, for the sulfur derivative, the internal bridging thiophene participates in a π‐electron conjugation

  捷径出击：报道了带有内部噻吩桥的核心修饰的内消旋芳基六卟啉的合成。噻吩桥改变电子结构以及π电子电路，从而在单寿命（增加的引入τ小号）和双光子吸收（TPA）截面。此外，对于硫衍生物，内部桥联噻吩参与π电子共轭途径。