4,4-difluoro-8-[4-(4,6-dichloro-1,3,5-triazin-2-ylamino)-phenyl]-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene | 1331914-85-2

• 英文名称: 4,4-difluoro-8-[4-(4,6-dichloro-1,3,5-triazin-2-ylamino)-phenyl]-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
• CAS: 1331914-85-2
• 化学式: C₂₂H₁₉BCl₂F₂N₆
• 分子量: 487.147
• InChiKey: MMTDIQFGQOBQMW-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  4,4-difluoro-8-[4-(4,6-dichloro-1,3,5-triazin-2-ylamino)-phenyl]-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  DiiodoBodipy-Rhodamine Dyads: Preparation and Study of the Acid-Activatable Competing Intersystem Crossing and Energy Transfer Processes

  摘要：

  Iodo-bodipy/rhodamine dyads with cyanuric chloride linker were prepared with the goal of achieving pH switching of the triplet excited state formation. The pH switching takes advantage of the acid-activated reversible cyclic lactam <-> opened amide transformation of the rhodamine unit and the fluorescence resonance energy transfer (FRET). The photophysical properties of the dyads were studied with steady-state and femtosecond/nanosecond time-resolved transient absorption spectroscopies, electrochemical methods, as well as TD-DFT calculations. Our results show that the model dyad is an efficient triplet state generator under neutral condition, when the rhodamine unit adopts the closed form. The triplet generation occurs at the iodo-bodipy moiety and the triplet state is long-lived, with a lifetime of 51.7 mu s. In the presence of the acid, the rhodamine unit adopts an opened amide form, and in this case, the efficient FRET occurs from iodo-bodipy to the rhodamine moiety. The FRET is much faster (tau(FRET) = 81 ps) than the intersystem crossing of iodo-bodipy (tau(ISC) = 178 ps), thus suppressing the triplet generation is assumed. However, we found that the additional energy transfer occurs at the longer timescale, which eventually converts the rhodamine-based S-1 state to the T-1 state localized on the iodo-bodipy unit.

  DOI：

  10.1021/jp509858t
• 作为产物：
  描述：

  三聚氯氰 、 8-(4-苯胺基)氟硼吡咯 在 K₂CO₃ 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到4,4-difluoro-8-[4-(4,6-dichloro-1,3,5-triazin-2-ylamino)-phenyl]-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Promising Fast Energy Transfer System via an Easy Synthesis: Bodipy–Porphyrin Dyads Connected via a Cyanuric Chloride Bridge, Their Synthesis, and Electrochemical and Photophysical Investigations

  摘要：

  The boron dipyrrin (Bodipy) chromophore was combined with either a free-base or a Zn porphyrin moiety (H2P and ZnP respectively), via an easy synthesis involving a cyanuric chloride bridging unit, yielding dyads Bodipy-H2P (4) and Bodipy-ZnP (5). The photophysical properties of Bodipy-H2P (4) and Bodipy-ZnP (5) were investigated by UV-Vis absorption and emission spectroscopy, cyclic voltammetry, and femtosecond transient absorption spectroscopy. The comparison of the absorption spectra and cyclic voltammograms of dyads Bodipy-H2P (4) and Bodipy-ZnP (5) with those of their model compounds Bodipy, H2P, and ZnP shows that the spectroscopic and electrochemical properties of the constituent chromophores are essentially retained in the dyads indicating negligible interaction between them in the ground state. In addition, luminescence and. transient absorption experiments show that excitation of the Bodipy unit in Bodipy-H2P (4) and Bodipy-ZnP (5) into its first singlet excited state results in rapid Bodipy to porphyrin energy transfer-k(4) = 2.9 x 10(10) s(-1) and k(s) = 2.2 x 10(10) s(-1) for Bodipy-H2P (4) and Bodipy-ZnP (5), respectively-generating the first porphyrin-based singlet excited state. The porphyrin-based singlet excited states give rise to fluorescence or undergo intersystem crossing to the corresponding triplet excited states. The title complexes could also be used as precursors for further substitution on the third chlorine atom on the cyanuric acid moiety.

  DOI：

  10.1021/ic201052k

文献信息

• A New Approach for the Photosynthetic Antenna-Reaction Center Complex with a Model Organized Around an<i>s</i>-Triazine Linker
  作者：Susanne Kuhri、Georgios Charalambidis、Panagiotis A. Angaridis、Theodore Lazarides、Georgia Pagona、Nikos Tagmatarchis、Athanassios G. Coutsolelos、Dirk M. Guldi

  DOI：10.1002/chem.201302632

  日期：2014.2.10

  electron‐donor/acceptor conjugates were investigated by using UV/Vis absorption and emission spectroscopy, cyclic voltammetry, and femtosecond transient absorption spectroscopy. Comparison of the absorption spectra and cyclic voltammograms of BDP‐H2P‐C60 and BDP‐ZnP‐C60 with those of BDP‐H2P, BDP‐ZnP and BDP‐C60, which were used as references, showed that the spectroscopic and electrochemical properties of the

  已经设计并合成了两种新的光合天线反应中心复合物的人工模拟物（BDP-H 2 P-C 60和BDP-ZnP-C 60）。所得的电子给体/受体共轭物包含卟啉（以其游离碱形式（H 2 P）或以锌金属配合物（ZnP）的形式），硼联吡啶（BDP）和具有作为取代基的全吡咯烷吡咯烷氮，乙二醇链终止于氨基C 60 -X-NH 2（X =间隔基）。在这两种情况下，三个不同的组件通过s-连接三嗪通过氰尿酰氯的逐步取代反应。除了简便合成，围绕中心三个光和氧化还原活性组分的星型布置S-三嗪单元允许彼此之间的直接相互作用，而相比之下，报道例子，其中三个部件被布置在线性时尚。通过使用紫外/可见吸收和发射光谱，循环伏安法和飞秒瞬态吸收光谱研究了所得电子供体/受体共轭物的能量和电子转移性质。BDP-H 2 P-C 60和BDP-ZnP-C 60与BDP-H 2的吸收光谱和循环伏安图的比较用作参考的P，BDP-ZnP和BDP-C