5,15-bis(4-carbomethoxyphenyl)-10,20-bis(4-methylphenyl)porphyrin | 57056-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 5,15-bis(4-carbomethoxyphenyl)-10,20-bis(4-methylphenyl)porphyrin
• 英文别名: 5,15-bis(4-methoxycarbonylphenyl)-10,12-bis(4-methylphenyl)porphyrin；5,15-Di(p-Methoxycarbonylphenyl)-10,20-di(p-methylphenyl)porphine；H₂-5,15-di(p-methoxycarbonylphenyl)-10,20-di(p-tolyl)porphyrin；5,15-Di-(4-carbomethoxyphenyl)-10,20-ditolylporphyrin；4,4'-(10,20-di-p-tolyl-21H,23H-porphine-5,15-diyl)-bis-benzoic acid dimethyl ester；5,15-[bis(4-tolyl)]-10,20-bis[4-(methoxycarbonyl)phenyl]-porphyrin
• CAS: 57056-44-7
• 化学式: C₅₀H₃₈N₄O₄
• 分子量: 758.876
• InChiKey: QWECJAOIFHGRGB-ZNSTUQKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.51
• 重原子数：
  58.0
• 可旋转键数：
  6.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  109.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,15-bis(4-carbomethoxyphenyl)-10,20-bis(4-methylphenyl)porphyrin 在 盐酸 、 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.17h， 生成 4-[(5Z,10Z,14Z,19Z)-15-(4-Hydroxymethyl-phenyl)-10,20-di-p-tolyl-porphyrin-5-yl]-benzoic acid methyl ester
  参考文献：
  名称：

  Driving Force and Electronic Coupling Effects on Photoinduced Electron Transfer in a Fullerene-based Molecular Triad¶

  摘要：

  Tuning thermodynamic driving force and electronic coupling through structural modifications of a carotene (C) porphyrin (P) fullerene (C-60) molecular triad has permitted control of five electron and energy transfer rate constants and two excited state lifetimes in order to prepare a high-energy charge-separated state by photoinduced electron transfer with a quantum yield of essentially unity (greater than or equal to 96%). Excitation of the porphyrin moiety of C-P-C-60 is followed by a combination of photoinduced electron transfer to give C-P.+-C-60(.-) and singlet-singlet energy transfer to yield C-P-C-1(60). The fullerene excited state accepts an electron from the porphyrin to also generate C-P.+-C-60(.-). Overall, this initial state is formed with a quantum yield of 0.97, Charge shift from the carotenoid to yield C.+-P-C-60(.-) is at least 60 times faster than recombination of C-P.+-C-60(.-), leading to the overall quantum yield near unity for the final state. Formation of a similar charge-separated species from the zinc analog of the triad with a yield of 40% is also observed. Charge recombination of C.+-P-C-60(.-) in 2-methyltetra-hydrofuran yields the carotenoid triplet state, rather than the ground state, Comparison of the results for this triad with those for related triads with different structural features provides information concerning the effects of driving force and electronic coupling on each of the electron transfer steps.

  DOI：

  10.1562/0031-8655(2000)072<0598:dfaece>2.0.co;2
• 作为产物：
  描述：

  对甲酰基苯甲酸甲酯 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 22.25h， 生成 5,15-bis(4-carbomethoxyphenyl)-10,20-bis(4-methylphenyl)porphyrin
  参考文献：
  名称：

  具有富勒烯配位的二价二茂铁-锌卟啉-BODIPY的超分子四联体：电荷稳定，光合天线-反应中心模拟物

  摘要：

  一种新型的光合作用-天线反应中心模型化合物，由BF 2螯合的二吡咯亚甲基（BODIPY）作为能量吸收天线，锌卟啉（ZnP）作为主要电子供体，二茂铁（Fc）作为空穴迁移剂和苯基咪唑官能化的全吡咯烷（C 60已合成并表征了作为电子受体的Im）。系统地进行了光吸收和发射，计算结构优化和循环伏安法研究，以建立每个实体在多步光化学反应中的作用。根据光学和氧化还原数据建立的能级图有助于识别不同的光化学事件。BODIPY的选择性激发导致有效的单线态能量转移到ZnP实体。从超高速电子转移1 ZNP *（形成或者作为单重态能量转移或直接激发的结果）或1 Ç 60所得到的Fc（C形成的协调的富勒烯* 60 。 - ZNP：IM。+）–飞秒瞬态吸收研究证明了BODIPY自由基离子对。随后空穴迁移到二茂铁实体导致在Fc + - （C 60 。 +进口：ZNP）-BODIPY自由基离子对，持续了7-15微秒，这取决

  DOI：

  10.1002/chem.201404671

文献信息

• Electronic energy harvesting multi BODIPY-zinc porphyrin dyads accommodating fullerene as photosynthetic composite of antenna-reaction center
  作者：E. Maligaspe、T. Kumpulainen、N. K. Subbaiyan、M. E. Zandler、H. Lemmetyinen、N. V. Tkachenko、F. D’Souza

  DOI：10.1039/c002757j

  日期：——

  Efficient electronic energy transfer (EET) in the newly synthesized dyads comprised of zinc porphyrin covalently linked to one, two or four numbers of boron dipyrrin (BDP) entities is investigated. Both steady-state and time-resolved emission as well as transient absorption studies revealed occurrence of efficient singlet–singlet energy transfer from BDP to zinc porphyrin with the time scale ranging between 28 and 48 ps. A decrease in time constants for energy transfer with increasing the number of BDP units is observed revealing better antenna effect of dyads bearing higher number of boron dipyrrin entities. Further, supramolecular triads to mimic the ‘antenna-reaction center’ functionality of photosynthetic reaction center have been successfully constructed by coordinating fulleropyrrolidine appended with an imidazole ligand to the zinc porphyrin. The structural integrity of the supramolecular triads was arrived by optical, computational and electrochemical studies. Free energy calculations revealed possibility of photoinduced electron transfer from singlet excited zinc porphyrin to fullerene, and the preliminary transient absorption studies involving pump–probe technique are supportive of occurrence of electron transfer from 1ZnP* to fullerene in the supramolecular triads.

  在新合成的二元体中，锌卟啉与一个、两个或四个硼二吡咯(BDP)单元共价连接，研究了高效的电子能量转移(EET)。稳态和时间分辨发射以及瞬态吸收研究都显示从BDP到锌卟啉的有效单态-单态能量转移发生，时间尺度在28到48皮秒之间。随着BDP单元数量的增加，能量转移的时间常数降低，显示出具有更高数量硼二吡咯单元的二元体具有更好的天线效应。此外，为了模拟光合反应中心的“天线-反应中心”功能，成功构建了超分子三元体，通过将带有咪唑配体的富勒烯吡咯烷与锌卟啉配位。通过光学、计算和电化学研究确认了超分子三元体的结构完整性。自由能计算揭示了从单态激发锌卟啉到富勒烯的光诱导电子转移的可能性，而初步的瞬态吸收研究涉及泵-探针技术，支持超分子三元体中从1ZnP*到富勒烯的电子转移的发生。
• Cyclic oligomers based on complementary Zn(ii) and Sn(iv)-porphyrins
  作者：Gerald A. Metselaar、Pablo Ballester、Javier de Mendoza

  DOI：10.1039/b902408p

  日期：——

  The aggregation of a 1 : 1 mixture of complementary Sn(IV)- and Zn(II)-porphyrins into cyclic decameric and dodecameric assemblies has been demonstrated by 1H NMR, GPC, DOSY and MALDI-TOF spectrometry.

  通过 1H NMR、GPC、DOSY 和 MALDI-TOF 光谱法，证明了互补 Sn(IV)- 和 Zn(II)-卟啉的 1 : 1 混合物聚集成环状十聚体和十二聚体。
• Synthesis of galactopyranosyl substituted porphyrins
  作者：Hermann K. Hombrecher、Stefan Ohm、Daniela Koll

  DOI：10.1016/0040-4020(96)00174-3

  日期：1996.4

  The synthesis of several galactopyranosyl substituted porphyrins is described. Starting from porphyrin carboxylic esters (1) di-O-isopropylidene-α-D-galactopyranosyl substituted porphyrins 3a – 3e were synthesised by a transesterification procedure. Treatment of 3a – 3e with TFA/water leads to the formation of galactopyranosyl substituted porphyrins 4a – 4e in excellent yield. Furthermore porphyrin

  描述了几种吡喃半乳糖基取代的卟啉的合成。从卟啉羧酸酯（1）开始，通过酯交换法合成了二-O-异亚丙基-α-D-吡喃半乳糖基取代的卟啉3a-3e。用TFA /水处理3a-3e可以形成产率极高的galactopyranosyl取代的卟啉4a-4e。此外，卟啉3e可以通过二-O-异亚丙基-α-D-吡喃半乳糖基取代的苯甲醛7与吡咯的反应来合成。通过CsF催化6-脱氧-6-溴-二-O-异亚丙基-α-D-吡喃半乳糖6的缩合反应合成醛7 用4-甲酰基苯甲酸。
• An efficient synthesis of tetraaryl porphyrins substituted with ester groups bearing long alkyl chains
  作者：Hermann K. Hombrecher、Stefan Ohm

  DOI：10.1016/s0040-4020(01)86323-7

  日期：1993.3

  The synthesis of tetraaryl porphyrins substituted with long chain ester groups is described. The compounds are conveniently prepared from the methyl ester 1a via a based induced transesterification procedure. The method is also applicable for the synthesis of ester linked diporphyrins.

  描述了被长链酯基取代的四芳基卟啉的合成。该化合物可通过基于基础的酯交换步骤，方便地由甲酯1a制备。该方法也适用于酯连接的双卟啉的合成。
• Synthesis and characterization of new acid-functionalized porphyrins displaying antimicrobial activity against gram positive bacteria, yeasts and filamentous fungi with or without ultra-high irradiance
  作者：Marc Sautour、Thibaut Théry、Gaëlle Divoux、Sébastien Dupont、Laurent Beney、Claude P. Gros、Nicolas Desbois

  DOI：10.1016/j.bmc.2024.117810

  日期：2024.7

  The antimicrobial activity of new acid-functionalized porphyrins, with or without ultra-high irradiance, was investigated. Antibacterial efficacy was evaluated against (methicillin-resistant or methicillin-sensitive strains) and antifungal efficacy was evaluated against the yeast and the filamentous fungi .

  研究了新型酸功能化卟啉在有或没有超高辐照度的情况下的抗菌活性。针对（甲氧西林抗性或甲氧西林敏感菌株）评估抗菌功效，并评估针对酵母和丝状真菌的抗真菌功效。