2-(9-anthranoyl)-7-tert-butyl-4,9-dibromo-10b,10c-dimethyl-trans-10b,10c-dihydropyrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(9-anthranoyl)-7-tert-butyl-4,9-dibromo-10b,10c-dimethyl-trans-10b,10c-dihydropyrene
• 英文别名: anthracen-9-yl-[(10bS,10cR)-4,9-dibromo-7-tert-butyl-10b,10c-dimethylpyren-2-yl]methanone
• 化学式: C₃₇H₃₀Br₂O
• 分子量: 650.453
• InChiKey: AKBHTLXHKDGTPC-AARKOHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  9-蒽甲酰氯 、 4,9-dibromo-2,7-di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以13%的产率得到2-(9-anthranoyl)-7-tert-butyl-4,9-dibromo-10b,10c-dimethyl-trans-10b,10c-dihydropyrene
  参考文献：
  名称：

  Oligothiophene Functionalized Dimethyldihydropyrenes I: Syntheses and Photochromicity

  摘要：

  The syntheses of 2,7-di-tert-butyldimethyldihydrobenzo[e]pyrenes with thienyl (6), terthienyl (7), and pentathienyl (14) side chains at the 4,5- positions, ter- and pentathienyl side chains at the 4-position with ter- (39) and pentathienylcarbonyl (40) side chains at the 10- and 11-positions, 2-naphthoyl-7-tert-butyldimethyldihydropyrenes with ter- (53), penta- (54), and septithienyl (55) side chains at the 4,9-positions are described. These compounds are all photochromic and open to the corresponding cyclophanedienes with long wavelength ( > 490 nm) light, and as such, the conjugative path could change considerably, making them suitable to investigate as potentially switchable conducting molecules. In this paper, the syntheses and the photochemical and thermal isomerizations are studied in the accompanying paper, the electrochemical and conductive properties are studied. Here, a comparison of the relative opening rates to that of the benzo[e]pyrene 4 (with no thienyl substituents) is made, and all of the above photochromes show considerably enhanced photo-opening of the DHPs to the CPDs. As examples, 14, 40, and 54 were cycled between the open and closed forms, and no decomposition was observed; however, when 54 was irradiated for 40 h with 254 nm light, some radicals did form, which enhanced the thermal closing rate, and so extensive irradiation with short wave UV is better avoided. The thermal closing reactions were also studied, and all of the above compounds close faster than benzo-CPD 4', though for the highly photochromic ter- and pentathienyl benzo-CPDs 39' and 40', the rate was not too enhanced from that of 4' and so are probably the best compromise between fast photochromicity and slow thermal reversion.

  DOI：

  10.1021/jo901070y

文献信息

• Oligothiophene Functionalized Dimethyldihydropyrenes I: Syntheses and Photochromicity
  作者：Stephen G. Robinson、Vittorio A. Sauro、Reginald H. Mitchell

  DOI：10.1021/jo901070y

  日期：2009.9.4

  The syntheses of 2,7-di-tert-butyldimethyldihydrobenzo[e]pyrenes with thienyl (6), terthienyl (7), and pentathienyl (14) side chains at the 4,5- positions, ter- and pentathienyl side chains at the 4-position with ter- (39) and pentathienylcarbonyl (40) side chains at the 10- and 11-positions, 2-naphthoyl-7-tert-butyldimethyldihydropyrenes with ter- (53), penta- (54), and septithienyl (55) side chains at the 4,9-positions are described. These compounds are all photochromic and open to the corresponding cyclophanedienes with long wavelength ( > 490 nm) light, and as such, the conjugative path could change considerably, making them suitable to investigate as potentially switchable conducting molecules. In this paper, the syntheses and the photochemical and thermal isomerizations are studied in the accompanying paper, the electrochemical and conductive properties are studied. Here, a comparison of the relative opening rates to that of the benzo[e]pyrene 4 (with no thienyl substituents) is made, and all of the above photochromes show considerably enhanced photo-opening of the DHPs to the CPDs. As examples, 14, 40, and 54 were cycled between the open and closed forms, and no decomposition was observed; however, when 54 was irradiated for 40 h with 254 nm light, some radicals did form, which enhanced the thermal closing rate, and so extensive irradiation with short wave UV is better avoided. The thermal closing reactions were also studied, and all of the above compounds close faster than benzo-CPD 4', though for the highly photochromic ter- and pentathienyl benzo-CPDs 39' and 40', the rate was not too enhanced from that of 4' and so are probably the best compromise between fast photochromicity and slow thermal reversion.