Continuous flow synthesis of meso-substituted porphyrins with inline UV–Vis analysis

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Flow Chemistry Pub Date : 2024-01-15 DOI:10.1007/s41981-023-00305-w
Firdaus Parveen, Henry J. Morris, Harvey West, Anna G. Slater
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Abstract

Porphyrin derivatives have found diverse applications due to their attractive photophysical and catalytic properties, but remain challenging to synthesize, particularly at scale. Porphyrin synthesis thus stands to benefit from the more controlled environment, opportunities for efficient optimization, and potential for scale-up available in flow. Here, we have transferred Lindsey porphyrin synthesis into flow, enabling controlled timing for oxidation and neutralization steps and real time monitoring of the reaction mixture with inline UV–Vis analysis. For tetraphenyl porphyrin (TPP), inline UV–Vis showed the presence of protonated TPP, formed due to residual acid. Thus, inline monitoring allowed optimization of the neutralization step to improve yield. Three further porphyrin substrates were produced in flow; in two cases, the yield from inline UV was significantly higher than the yield from post-purification, identifying further yield losses that could be recovered by modifying the purification step. The workflow presented here can be adapted to multiple substrates to systematically optimise porphyrin yield, reducing the time needed to develop scalable routes to these valuable compounds.

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利用在线紫外可见光分析连续流合成介取代卟啉
卟啉衍生物因其极具吸引力的光物理和催化特性而被广泛应用,但其合成仍然具有挑战性,尤其是大规模合成。因此,卟啉合成将受益于流动中更受控的环境、高效优化的机会和规模化的潜力。在这里,我们将林赛卟啉的合成转移到了流动中,实现了氧化和中和步骤的时间控制,并通过在线紫外可见光分析对反应混合物进行实时监控。对于四苯基卟啉 (TPP),在线紫外可见光谱分析显示了由于残留酸而形成的质子化 TPP 的存在。因此,在线监测可以优化中和步骤,提高产率。在流动过程中又生产出了三种卟啉底物;在其中两种情况下,在线紫外检测的产率明显高于后纯化的产率,从而确定了可通过修改纯化步骤挽回的进一步产率损失。本文介绍的工作流程可适用于多种底物,以系统地优化卟啉产量,从而缩短开发这些有价值化合物的可扩展路线所需的时间。
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来源期刊
Journal of Flow Chemistry
Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
6.40
自引率
3.70%
发文量
29
审稿时长
>12 weeks
期刊介绍: The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
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