Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin,Organic & Biomolecular Chemistry

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Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-10-09 , DOI: 10.1039/c8ob02150c
Joffrey Pijeat _{1,

2,

3,

4,

5} , Yannick J. Dappe _{3,

4,

5,

6,

7} , Pierre Thuéry _{2,

3,

4,

5,

8} , Stéphane Campidelli _{1,

2,

3,

4,

5}

Affiliation

The outstanding properties of porphyrins and the extreme versatility of their synthesis and their functionalisation constitute real assets for the fabrication of opto- and electroactive materials or for biological applications. In the large collection of porphyrinic structures, meso-substituted anthracenylporphyrins are among the less studied. Here, we synthesised the 5,10,15,20-tetra-bromoanthracenylporphyrin (BrTAP) and we investigated its chemical reactivity by post-synthetic modification using Suzuki–Miyaura cross coupling reactions with a series of boronic acids to generate a collection of original tetra-anthracenyl porphyrin based molecules: tetraphenylanthracenylporphyrin (TPAP), tetratolylanthracenylporphyrin (TTAP), tetramethoxyphenylanthracenylporphyrin (TMPAP), tetranaphthylanthracenylporphyrin (TNAP) and tetrapyrenylanthracenylporphyrin (TPyAP). Optical characterisations of these modified porphyrins showed, in most cases, only emission of the porphyrin in the visible region with extinction of the fluorescence of PAHs in the UV or visible region.

中文翻译：

合成和Suzuki-Miyaura交叉偶联反应用于四溴蒽基卟啉的合成后修饰

卟啉的卓越性能以及其合成和功能化的极强多功能性，构成了制造光敏和电活性材料或生物应用的真正资产。在大量的卟啉结构中，内消旋取代的蒽基卟啉是研究较少的化合物之一。在这里，我们合成了5,10,15,20-四溴蒽基卟啉（BrTAP），并通过使用铃木-宫浦交叉偶联反应与一系列硼酸的合成后改性方法研究了其化学反应性，从而产生了一系列原始四氢呋喃-蒽基卟啉基分子：四苯基蒽基卟啉（TPAP），四甲苯基蒽基卟啉（TTAP），四甲氧基苯基蒽基卟啉（TMPAP），四萘基蒽基卟啉（TNAP）和四吡喃基蒽基卟啉（TPyAP）。在大多数情况下，这些修饰的卟啉的光学表征表明，仅卟啉在可见光区域发射，而在紫外或可见光区域PAHs的荧光消失。

更新日期：2018-11-07

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