10-(4-((2-ethylhexyl)oxy)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium | 1304574-81-9

• 英文名称: 10-(4-((2-ethylhexyl)oxy)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
• CAS: 1304574-81-9
• 化学式: C₂₇H₃₅BF₂N₂O
• 分子量: 452.396
• InChiKey: OPCQIEUYNCZDPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  10-(4-((2-ethylhexyl)oxy)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium 在 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 二异丙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 10-(4-((2-ethylhexyl)oxy)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-2,8-bis((trimethylsilyl)ethynyl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  BODIPY-Based Donor–Acceptor π-Conjugated Alternating Copolymers

  摘要：

  Four novel pi-conjugated copolymers incorporating 4,4-difluoro-4-borata-3a-azonia-4a-aza-s-indacene (BODIPY) core as the "donor" and quinoxaline (Qx), 2,1,3-benzothiadiazole (BzT), N,N'-di(2'-ethyl)hexyl-3,4,7,8-naphthalenetetracarboxylic diimide (NDI), and N,N'-di(2'-ethyl)hexyl-3,4,9,10-perylene tetracarboxylic diimide (PDI) as acceptors were designed and synthesized via Sonogashira polymerization. The polymers were characterized by H-1 NMR spectroscopy, gel permeation chromatography (GPC), UV-vis absorption spectroscopy, and cyclic voltammetry. Density functional theory (DFT) calculations were performed on polymer repeat units, and the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels were estimated from the optimized geometry using B3LYP functional and 6-311g(d,p) basis set. Copolymers with Qx and BzT possessed HOMO and LUMO energy levels comparable to those of BODIPY homopolymer, while PDI stabilized both HOMO and LUMO levels. Semiconductor behavior of these polymers was estimated in organic thin-film transistors (OTFT). While the homopolymer, Qx, and BzT-based copolymers showed only p-type semiconductor behavior, copolymers with PDI and NDI showed only n-type behavior.

  DOI：

  10.1021/ma200839q
• 作为产物：
  描述：

  2,4-二甲基吡咯 在 三氟化硼乙醚 、 三乙胺 、 三氟乙酸 、 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 3.08h， 生成 10-(4-((2-ethylhexyl)oxy)phenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  BODIPY-Based Donor–Acceptor π-Conjugated Alternating Copolymers

  摘要：

  Four novel pi-conjugated copolymers incorporating 4,4-difluoro-4-borata-3a-azonia-4a-aza-s-indacene (BODIPY) core as the "donor" and quinoxaline (Qx), 2,1,3-benzothiadiazole (BzT), N,N'-di(2'-ethyl)hexyl-3,4,7,8-naphthalenetetracarboxylic diimide (NDI), and N,N'-di(2'-ethyl)hexyl-3,4,9,10-perylene tetracarboxylic diimide (PDI) as acceptors were designed and synthesized via Sonogashira polymerization. The polymers were characterized by H-1 NMR spectroscopy, gel permeation chromatography (GPC), UV-vis absorption spectroscopy, and cyclic voltammetry. Density functional theory (DFT) calculations were performed on polymer repeat units, and the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels were estimated from the optimized geometry using B3LYP functional and 6-311g(d,p) basis set. Copolymers with Qx and BzT possessed HOMO and LUMO energy levels comparable to those of BODIPY homopolymer, while PDI stabilized both HOMO and LUMO levels. Semiconductor behavior of these polymers was estimated in organic thin-film transistors (OTFT). While the homopolymer, Qx, and BzT-based copolymers showed only p-type semiconductor behavior, copolymers with PDI and NDI showed only n-type behavior.

  DOI：

  10.1021/ma200839q

文献信息

• Self-reporting heavy atom-free photodynamic therapy agents
  作者：Gulsen Turkoglu、Gozde Kayadibi Koygun、Mediha Nur Zafer Yurt、Naime Demirok、Sundus Erbas-Cakmak

  DOI：10.1039/d0ob01944e

  日期：——

  self-reporting distyryl BODIPY-based photodynamic therapy agents functionalized with singlet oxygen responsive imidazole and tertiary amine moieties are developed. Heavy atom-free photosensitizers are demonstrated to have efficient photodynamic action in MCF7 cells. The fluorescence intensity of the photosensitizers is shown to be reduced as a result of 1O2 generation without any significant change

  开发了两种新型、基于二苯乙烯基 BODIPY 的新型光动力治疗剂，这些药物用单线态氧响应性咪唑和叔胺部分功能化。已证明无重原子光敏剂在 MCF7 细胞中具有有效的光动力作用。光敏剂的荧光强度显示为由于1 O 2的产生而降低，而光动力活性没有任何显着变化。
• Selective photosensitization through an AND logic response: optimization of the pH and glutathione response of activatable photosensitizers
  作者：Sundus Erbas-Cakmak、Fatma Pir Cakmak、Seda Demirel Topel、Taha Bilal Uyar、Engin U. Akkaya

  DOI：10.1039/c5cc01261a

  日期：——

  A molecular AND logic gate, which is an activatable photosensitizer, requires above-threshold values of acidity (pH) and GSH for full activity.

  一个分子AND逻辑门，即一种可激活的光敏剂，需要超过阈值的酸性（pH）和GSH才能发挥全部活性。

• Coupled Oscillators for Tuning Fluorescence Properties of Squaraine Dyes
  作者：Christoph Lambert、Thorsten Scherpf、Harald Ceymann、Alexander Schmiedel、Marco Holzapfel

  DOI：10.1021/ja512338w

  日期：2015.3.18

  Combining a squaraine (S) and a BODIPY (B) chromophore in a heterodimer (SB) and two heterotrimers (BSB and SBS) by alkyne bridges leads to the formation of coupled oscillators whose fluorescence properties are superior compared to the parent squaraine chromophore. The lowest energy absorption and emission properties of these superchromophores are mainly governed by the squaraine part and are shifted

  通过炔桥将异源二聚体 (SB) 和两个异源三聚体 (BSB 和 SBS) 中的方酸 (S) 和 BODIPY (B) 生色团结合导致形成耦合振荡器，其荧光特性优于母方方酸生色团。这些超发色团的最低能量吸收和发射特性主要由方酸部分控制，并通过方酸和 BODIPY 染料之间的激子相互作用向红色移动超过 1000 cm(-1)。采用偏振相关瞬态吸收和荧光上转换测量，我们可以证明 SB 和 BSB 中最低的能量吸收是由单个激子态引起的，而 SBS 是由两个激子态引起的。尽管它们的最低吸收带发生光谱红移，与母方方酸根发色团 SQA 相比，SB 和 BSB 的荧光量子产率增加。这是由于从 BODIPY 状态借用强度引起的，与 SQA 相比，它使 SB 的最低能带的平方跃迁矩显着增加了 29%，BSB 的跃迁矩增加了 63%。因此，激子耦合导致 SB 的荧光量子产率显着增强 26%，BSB 的荧光量子产率显着增强