8,9-dibromo-1-formyl-5-(4-(methoxycarbonyl)phenyl)dipyrromethane

• 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: 8,9-dibromo-1-formyl-5-(4-(methoxycarbonyl)phenyl)dipyrromethane
• 英文别名: 8,9-dibromo-5-[(4-methoxycarbonyl)phenyl]dipyrromethane；methyl 4-[(4,5-dibromo-1H-pyrrol-2-yl)-(5-formyl-1H-pyrrol-2-yl)methyl]benzoate
• 化学式: C₁₈H₁₄Br₂N₂O₃
• 分子量: 466.129
• InChiKey: BNRHVCDBHTYYJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8,9-dibromo-1-formyl-5-(4-(methoxycarbonyl)phenyl)dipyrromethane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.17h， 生成
  参考文献：
  名称：

  [EN] PORPHYRIN-HYDROPORPHYRIN COMPOUNDS, COMPOSITIONS COMPRISING THE SAME AND METHODS OF USE THEREOF
  [FR] COMPOSÉS DE PORPHYRINE-HYDROPORPHYRINE, COMPOSITIONS LES COMPRENANT ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  Described herein are compounds that include a first porphyrin; and a first hydroporphyrin, wherein the first porphyrin is attached to the first hydroporphyrin. The compound may be a luminescent compound (e.g., a fluorescent compound). Also provided are particles and compositions including compounds described herein. Further provided are methods of making and using the particles and methods of making the same.

  公开号：

  WO2022216927A1
• 作为产物：
  描述：

  对甲酰基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 2.83h， 生成 8,9-dibromo-1-formyl-5-(4-(methoxycarbonyl)phenyl)dipyrromethane
  参考文献：
  名称：

  NARROW EMISSION DYES, COMPOSITIONS COMPRISING SAME, AND METHODS FOR MAKING AND USING SAME

  摘要：

  Provided are chlorin derivatives with narrow band emission. In some embodiments, the bacteriochlorin derivatives are PEGylated. In some embodiments, the chlorin derivatives have high water solubility (e.g., 10 mg/mL or more). In some embodiments, the chlorin derivatives are PEGylated and have high water solubility. The chlorin derivatives can include bioconjugatable groups for forming conjugates, for example, with antibodies and nanoparticles. The chlorin derivatives and their conjugates can be used in imaging and therapeutic applications. Methods of synthesizing the chlorin derivatives are also provided.

  公开号：

  US20220249707A1

文献信息

• Near-IR Emissive Chlorin–Bacteriochlorin Energy-Transfer Dyads with a Common Donor and Acceptors with Tunable Emission Wavelength
  作者：Zhanqian Yu、Marcin Ptaszek

  DOI：10.1021/jo4016858

  日期：2013.11.1

  Excitation of the chlorin donor results in relatively strong emission of the bacteriochlorin acceptor, with a quantum yield Φf range of 0.155–0.23 in toluene and 0.12–0.185 in DMF. The narrow, tunable emission band of bacteriochlorins enables the selection of a series of three dyads with well-resolved emissions at 732, 760, and 788 nm, and common excitation at 645 nm. Selected dyads have been also converted

  设计，合成和光学性质的一系列新型二氢卟酚-细菌二氢卟啉能量转移二元组。每个二联体由一个普通的吸收红光（645-646 nm）的二氢卟酚作为能量供体，以及一个不同的近红外发射细菌二氢卟酚作为能量受体。每个细菌绿素受体都配备有不同的一组辅助色素，因此它们各自以不同的波长发射。即使对于二氢卟酚-细菌二氢卟吩对，在供体发射和受体吸收之间有较大的间隔（最高达122 nm）时，二联体也显示出有效的能量转移（≥0.77）。在菌绿素受体的相对较强的发射的二氢卟酚供体的结果激发，具有量子产率Φ ˚F甲苯为0.155–0.23，DMF为0.12–0.185。细菌绿素的窄且可调的发射带使得能够选择一系列三个双色组，它们在732、760和788 nm处具有良好分辨的发射，并在645 nm处具有共同的激发。选定的二元组也已转化为可生物缀合的N-琥珀酰胺酯衍生物。所述二元组的光学性质使其成为开发近红外荧光团以同时成像
• Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins
  作者：Mengran Liu、Chih-Yuan Chen、Amit Kumar Mandal、Vanampally Chandrashaker、Rosemary B. Evans-Storms、J. Bruce Pitner、David F. Bocian、Dewey Holten、Jonathan S. Lindsey

  DOI：10.1039/c6nj01154c

  日期：——

  designs have been developed wherein stable synthetic chlorins – analogues of chlorophylls – have been tailored with PEG groups for use in aqueous solution. The designs differ with regard to order of the installation (pre/post-formation of the chlorin macrocycle) and position of the PEG groups. Six PEGylated synthetic chlorins (three free bases, three zinc chelates) have been prepared, of which four

  在红色光谱区域（600-700 nm）吸收和发射，可溶于水并带有可生物缀合的系链的发色团相对稀少，但可以满足光化学和光医学领域的许多应用。在这里，已经开发出了三种分子设计，其中稳定的合成二氢卟酚（叶绿素的类似物）已被PEG基团定制用于水溶液。设计在安装顺序（二氢卟酚大环的预/后形成）和PEG基团的位置方面有所不同。已制备了六种PEG化的合成二氢卟酚（三个游离碱，三个锌螯合物），其中四个装有可生物缀合的（羧酸）系链。水性增溶最有效的设计需要面部护理，其中PEG基团突出于疏水盘状二氢卟酚大环平面的上方和下方。二氢卟酚在〜400 nm（B波段）和红色区域（Qy乐队）；无论激发的波长如何，发射都发生在红色区域。因此，在约400 nm范围内进行激励可提供大于200 nm的有效斯托克斯位移。四种可生物共轭的水溶性二氢卟酚在水中在613 / 614、636 / 638、698 / 700和706/710
• Deep-Red Emissive BODIPY–Chlorin Arrays Excitable with Green and Red Wavelengths
  作者：Adam Meares、Andrius Satraitis、Nithya Santhanam、Zhanqian Yu、Marcin Ptaszek

  DOI：10.1021/acs.joc.5b00119

  日期：2015.4.17

  We report here the synthesis and characterization of BODIPY-chlorin arrays containing a chlorin subunit, with tunable deep-red (641-685 nm) emission, and one or two BODIPY moieties, absorbing at 504 nm. Two types of arrays were examined: one where BODIPY moieties are attached through a phenylacetylene linker at the 13- or 3,13-positions of chlorin, and a second type where BODIPY is attached at the 10-position of chlorin through an amide linker. Each of the examined arrays exhibits an efficient (>= 0.80) energy transfer from BODIPY to the chlorin moiety in both toluene and DMF and exhibits intense fluorescence of chlorin upon excitation of BODIPY at similar to 500 nm. Therefore, the effective Stokes shift in such arrays is in the range of 140-180 nm. Dyads with BODIPY attached at the 10-position of chlorin exhibit a bright fluorescence in a range of solvents with different polarities (i.e., toluene, MeOH, DMF, and DMSO). In contrast to this, some of the arrays in which BODIPY is attached at the 3- or at both 3,13-positons of chlorin exhibit significant reduction of fluorescence in polar solvents. Overall, dyads where BODIPY is attached at the 10-position of chlorin exhibit similar to 5-fold brighter fluorescence than corresponding chlorin monomers, upon excitation at 500 nm.