2,8-di(4-methoxyphenyl)-11-trifluoromethyl-difuro[2,3-b]-[3,2-g]-5,5-difluoro-5-bora-3a,4a-diaza-s-indacene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 英文名称: 2,8-di(4-methoxyphenyl)-11-trifluoromethyl-difuro[2,3-b]-[3,2-g]-5,5-difluoro-5-bora-3a,4a-diaza-s-indacene
• 英文别名: (4-MeO-Ph)2(CF3)C13H4O2N2BF2；(T-4)-Difluoro[2-(4-methoxyphenyl)-5-[2,2,2-trifluoro-1-[2-(4-methoxyphenyl)-5H-furo[3,2-b]pyrrol-5-ylidene-KappaN4]ethyl]-4H-furo[3,2-b]pyrrolato-KappaN4]boron；2,2-difluoro-6,16-bis(4-methoxyphenyl)-11-(trifluoromethyl)-7,15-dioxa-3-aza-1-azonia-2-boranuidapentacyclo[10.6.0.03,10.04,8.014,18]octadeca-1(18),4(8),5,9,11,13,16-heptaene
• 化学式: C₂₈H₁₈BF₅N₂O₄
• 分子量: 552.265
• InChiKey: HIHVCWVLLXKIRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  40
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,8-di(4-methoxyphenyl)-11-trifluoromethyl-difuro[2,3-b]-[3,2-g]-5,5-difluoro-5-bora-3a,4a-diaza-s-indacene 在 溴 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以52%的产率得到3,7-dibromo-2,8-di(4-methoxyphenyl)-11-trifluoromethyl-difuro[2,3-b]-[3,2-g]-5,5-difluoro-5-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Singlet Oxygen Generation by Novel NIR BODIPY Dyes

  摘要：

  Five novel near-infrared BODIPY dyes were prepared for improved singlet oxygen generation using thiophene and bromine. Theoretical, optical, photostable, and singlet oxygen generation characteristics of these dyes were assessed. Predicted excitation energies by TDDFT calculations were in good agreement (Delta E approximate to 0.06 eV) with experimental data. All five dyes showed both excitation and emission In the NIR range. In particular, two dyes having sulfur and bromine atoms showed efficient singlet oxygen generation with high photostability.

  DOI：

  10.1021/ol2014076
• 作为产物：
  描述：

  2-(4-methoxyphenyl)-5-[2,2,2-trifluoro-1-[2-(4-methoxyphenyl)-4H-furo[3,2-b]pyrrol-5-yl]ethylidene]furo[3,2-b]pyrrole 在 三氟化硼乙醚 、 三乙胺 作用下， 生成 2,8-di(4-methoxyphenyl)-11-trifluoromethyl-difuro[2,3-b]-[3,2-g]-5,5-difluoro-5-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Singlet Oxygen Generation by Novel NIR BODIPY Dyes

  摘要：

  Five novel near-infrared BODIPY dyes were prepared for improved singlet oxygen generation using thiophene and bromine. Theoretical, optical, photostable, and singlet oxygen generation characteristics of these dyes were assessed. Predicted excitation energies by TDDFT calculations were in good agreement (Delta E approximate to 0.06 eV) with experimental data. All five dyes showed both excitation and emission In the NIR range. In particular, two dyes having sulfur and bromine atoms showed efficient singlet oxygen generation with high photostability.

  DOI：

  10.1021/ol2014076

文献信息

• RESIN COMPOSITION AND MOLDED ARTICLE
  申请人：DIC CORPORATION

  公开号：US20160271273A1

  公开（公告）日：2016-09-22

  The invention contains a resin and a near infrared fluorescent material which is one type or two or more types of compounds selected from General Formulas (I 1 ) to (I 4 ) and has a maximum fluorescence wavelength of 650 nm or longer. In Formulas, R a and R b , R c and R d , R h and R i , and R j and R k form rings together with the nitrogen atom to which R a , R c , R h , and R j are bonded; R e and R f represent a halogen atom or an oxygen atom; each of R l , R m , R n , and R o independently represents a halogen atom, a C 1-20 alkyl group, a C 1-20 alkoxy group, an aryl group, or a heteroaryl group; R g , R r , and R s represent a hydrogen atom or an electron withdrawing group; and each of R p and R q independently represents a hydrogen atom, a halogen atom, a C 1-20 alkyl group, a C 1-20 alkoxy group, an aryl group, or a heteroaryl group.

  该发明包含树脂和一种近红外荧光材料，该材料是从通用式(I1)到(I4)中选择的一种或两种或更多种化合物，并且具有最大荧光波长为650纳米或更长。在公式中，Ra和Rb，Rc和Rd，Rh和Ri，以及Rj和Rk与它们结合的氮原子一起形成环；Re和Rf代表卤素原子或氧原子；Rl、Rm、Rn和Ro分别独立表示卤素原子、C1-20烷基基团、C1-20烷氧基团、芳基或杂环芳基；Rg、Rr和Rs代表氢原子或电子吸引基团；Rp和Rq中的每一个独立表示氢原子、卤素原子、C1-20烷基基团、C1-20烷氧基团、芳基或杂环芳基。
• Small Molecule Near-Infrared Boron Dipyrromethene Donors for Organic Tandem Solar Cells
  作者：Tian-yi Li、Toni Meyer、Zaifei Ma、Johannes Benduhn、Christian Körner、Olaf Zeika、Koen Vandewal、Karl Leo

  DOI：10.1021/jacs.7b07887

  日期：2017.10.4

  Three furan fused boron dipyrromethenes (BODIPYs) with a CF3 group on the meso-carbon are synthesized as near-infrared absorbing materials for vacuum processable organic solar cells. The best single junction device reaches a short-circuit current (jsc) of 13.3 mA cm–2 and a power conversion efficiency (PCE) of 6.1%. These values are highly promising for an electron donor material with an absorption

  三个呋喃稠硼dipyrromethenes（BODIPYs）与CF 3基团的内消旋-碳被合成为用于真空处理的有机太阳能电池的近红外线吸收材料。最佳的单结器件的短路电流（j sc）为13.3 mA cm -2，功率转换效率（PCE）为6.1％。这些值对于吸收起始超过900nm的电子供体材料是非常有前途的。在包括NIR BODIPY子电池和匹配的“绿色”吸收器子电池的串联太阳能电池中，实现了互补吸收，结果PCE约为10％。
• Boron dipyrromethene (BODIPY) with <i>meso</i>-perfluorinated alkyl substituents as near infrared donors in organic solar cells
  作者：Tian-yi Li、Johannes Benduhn、Yue Li、Frank Jaiser、Donato Spoltore、Olaf Zeika、Zaifei Ma、Dieter Neher、Koen Vandewal、Karl Leo

  DOI：10.1039/c8ta06261g

  日期：——

  Three furan-fused BODIPYs were synthesized with perfluorinated alkyl substitutes on the meso-C. As NIR absorbers, a PCE of 6.4% was achieved in a single junction organic solar cell with relatively low energy losses.

  三种嵌合呋喃环的BODIPY化合物被合成，其中在meso-C位置上具有全氟烷基取代基团。作为近红外吸收剂，在单结有机太阳能电池中实现了6.4%的光电转换效率，并且能量损失相对较低。
• Bright, Color-Tunable Fluorescent Dyes in the Visible−Near-Infrared Region
  作者：Keitaro Umezawa、Yuki Nakamura、Hiroshi Makino、Daniel Citterio、Koji Suzuki

  DOI：10.1021/ja077756j

  日期：2008.2.6

  Keio Fluors, which are based on boron-dipyrromethene (BDP), have excellent and useful optical properties: vivid colors and sharp emission in the visible−near-infrared region (583−738 nm), high quantum yields (Φ: 0.56−0.98), high extinction coefficients (185000−288000 M-1 cm-1), and good photostabilities. These optical properties are superior to many of the existing fluorescent dyes such as rhodamines,

  新合成的 Keio Fluors 基于硼-二吡咯亚甲基 (BDP)，具有出色且有用的光学特性：在可见光-近红外区域 (583-738 nm) 中呈现鲜艳的色彩和锐利的发射，高量子产率 (Φ: 0.56−0.98)、高消光系数 (185000−288000 M-1 cm-1) 和良好的光稳定性。这些光学特性优于许多现有的荧光染料，例如罗丹明、花青或其他基于 BDP 的荧光染料。
• FLUORESCENT COMPOUND AND LABELING AGENT COMPRISING THE SAME
  申请人：Keio University

  公开号：EP2022794B1

  公开（公告）日：2017-08-23