<br>共价连接的(BODIPY)2-3-吡咯基BODIPY三联体的合成与研究,Dalton Transactions

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共价连接的(BODIPY)2-3-吡咯基BODIPY三联体的合成与研究
Dalton Transactions ( IF 3.5 ) Pub Date : 2024-06-12 , DOI: 10.1039/d4dt01356e
Abani Sarkar ₁ , Kanhu Charan Behera ₁ , Mangalampalli Ravikanth ₁

Affiliation

使用内消旋-(对甲酰基苯基)-3-吡咯基BODIPY作为关键前体，通过一系列步骤合成了两个含有一个3-吡咯基BODIPY单元和两个BODIPY单元的新型共价连接三联体。通过使用 HRMS、一维和二维核磁共振波谱、X 射线晶体学、吸收、稳态和时间分辨荧光、循环伏安法和 DFT/TD-DFT 技术，对这两个三元组进行了彻底的表征和研究。这些三元组的X射线结构分析表明，内消旋-BODIPY和3-吡咯基BODIPY的二吡啉单元在同一平面上取向，而α-BODIPY单元的二吡啉单元几乎垂直于3-吡咯基BODIPY的取向博迪单位。两个三元组在 510-675 nm 区域均显示出两个分离良好的吸收带，对应于 BODIPY 和 3-吡咯基 BODIPY 单元。在这些三元组中，BODIPY单元在较高能量区域吸收并充当能量供体，而3-吡咯基BODIPY单元在较低能量区域吸收并充当能量受体。这些三元组的稳态和时间分辨荧光研究表明，在选择性激发两个三元组中的 BODIPY 单元时，从 BODIPY 单元到 3-吡咯基 BODIPY 单元的分子内单线态-单线态能量转移的效率接近 98%。 DFT 和 TD-DFT 研究证实了实验结果。

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Synthesis and studies of covalently linked (BODIPY)2-3-pyrrolyl BODIPY triads

Two novel covalently linked triads containing one 3-pyrrolyl BODIPY unit and two BODIPY units were synthesized over a sequence of steps using meso-(p-formylphenyl)-3-pyrrolyl BODIPY as a key precursor. Both triads were thoroughly characterized and studied by using HRMS, 1D and 2D NMR spectroscopy, X-ray crystallography, absorption, steady-state and time-resolved fluorescence, cyclic voltammetry, and DFT/TD-DFT techniques. X-ray structural analysis of these triads revealed that the dipyrrin units of both meso-BODIPY and 3-pyrrolyl BODIPY were oriented in the same plane whereas the dipyrrin unit of the α-BODIPY unit was oriented almost perpendicular to that of the 3-pyrrolyl BODIPY unit. Both triads showed two well-separated absorption bands corresponding to BODIPY and 3-pyrrolyl BODIPY units in the 510–675 nm region. In these triads, the BODIPY unit absorbs in the higher energy region and acts as an energy donor whereas the 3-pyrrolyl BODIPY unit absorbs in the lower energy region and acts as an energy acceptor. Steady-state and time-resolved fluorescence studies of these triads indicated the possibility of intramolecular singlet–singlet energy transfer with almost 98% efficiency from the BODIPY units to the 3-pyrrolyl BODIPY unit upon selective excitation of the BODIPY unit in both triads. DFT and TD-DFT investigations corroborated the experimental findings.

更新日期：2024-06-12

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