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首页> 外文期刊>ChemPlusChem >Efficient Synthesis of Arylenedioxy‐Bridged Porphyrin Dimers through Catalyst‐Free Nucleophilic Aromatic Substitution
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Efficient Synthesis of Arylenedioxy‐Bridged Porphyrin Dimers through Catalyst‐Free Nucleophilic Aromatic Substitution

机译：通过无催化剂亲核芳族取代的高效合成亚氮杂桥桥卟啉二聚体

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摘要

Abstract A series of porphyrin dimers bridged by one or two rigid arylenedioxy linkers was successfully synthesized by catalyst‐free meso ‐aryloxylation involving nucleophilic aromatic substitution. The orientational freedom and conformation of the two porphyrin macrocycles in the mono‐bridged dimers depended on the steric hindrance between the macrocycles and substituents on the arylenedioxy linkers. On the other hand, the bis‐bridged dimers exhibited a highly rigid cofacial conformation with a distinct interplanar distance. The fluorescence quantum yields of the bis‐bridged dimers ( Φ fl =0.094 and 0.096) were quite similar to those of the monomers ( Φ fl =0.13). Owing to their high rigidities, the nonradiative deactivation of the photoexcited states associated with dimerization, which are observed for reported dimers, are mostly suppressed, thus suggesting that those dimers have highest rigidities among the cofacial porphyrin dimers exploring emission properties. Cyclic voltammetry revealed the electronic communication between the porphyrin macrocycles in the closely stacked bis‐bridged dimer.
机译：摘要通过涉及亲核芳族取代的催化剂的甲酚，成功地合成了一系列由一个或两个刚性亚氧化氧基接头的卟啉二聚体。单桥二聚体中的两个卟啉宏γ的取向自由度和构象依赖于亚丙糖接头上的宏茂剂和取代基之间的空间障碍。另一方面，双桥二聚体具有具有明显的横向距离的高度刚性的凝固构象。双桥二聚体（φF1= 0.094和0.096）的荧光量子产率与单体（φFL= 0.13）非常相似。由于其高刚性，主要抑制了与报告二聚体观察到的与二聚化相关的光屏蔽状态的非抗激活，因此表明这些二聚体在探索排放特性的巨孔卟啉二聚体中具有最高的刚性。循环伏安显示在紧密堆叠的双桥二聚体中的卟啉宏γ之间的电子通信。

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