Quantifying Environmental Effects on the Solution and Solid-State Stability of a Phenothiazine Radical Cation,Chemistry of Materials

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Quantifying Environmental Effects on the Solution and Solid-State Stability of a Phenothiazine Radical Cation
Chemistry of Materials ( IF 7.2 ) Pub Date : 2020-02-21 , DOI: 10.1021/acs.chemmater.9b05345
Aman Preet Kaur _{1,

2} , Oliver C. Harris ₃ , N. Harsha Attanayake _{1,

2} , Zhiming Liang ₁ , Sean R. Parkin ₁ , Maureen H. Tang ₃ , Susan A. Odom _{1,

2}

Affiliation

Organic radical cations are important intermediates in a wide variety of chemical processes. To date, significant progress has been made to improve the stability of these charged materials for use in electrochemical energy storage applications, especially in redox flow batteries. Here, we report the synthesis and isolation of four radical cation salts of N-(2-(2-methoxyethoxy)ethyl)phenothiazine (MEEPT), synthesizing MEEPT-X where X is tetrafluoroborate (BF₄^–), hexafluorophosphate (PF₆^–), perchlorate (ClO₄^–), and bis(trifluoromethanesulfonyl)imide (TFSI^–), and a comparison of their stability in solution and in the solid state. In the solution, UV–vis spectroscopy and rotating ring-disk electrode voltammetry show similar stability trends with respect to anion identity, with the TFSI^– salt being the most stable. In the solid state, these compounds show remarkable stability in air and at elevated temperatures, with the ClO₄^– salt surviving after being heated at 90 °C overnight in air. The different trends in MEEPT-X stability with X highlight the importance of concentration and the environment on the overall stability.

中文翻译：

量化对吩噻嗪自由基阳离子的溶液和固态稳定性的环境影响

有机自由基阳离子是许多化学过程中的重要中间体。迄今为止，已经在改善用于电化学能量存储应用，尤其是氧化还原液流电池中的这些带电材料的稳定性方面取得了重大进展。在这里，我们报告了N-（2-（2-甲氧基乙氧基）乙基）吩噻嗪（MEEPT）的四种自由基阳离子盐的合成和分离，合成了MEEPT-X，其中X是四氟硼酸盐（BF ₄^–），六氟磷酸盐（PF ₆^–），高氯酸盐（ClO ₄^–）和双（三氟甲磺酰基）酰亚胺（TFSI ^–），并比较它们在溶液和固态下的稳定性。在溶液中，紫外可见光谱和旋转环盘电极伏安法在阴离子特性方面显示出相似的稳定性趋势，其中TFSI ^–盐最稳定。在固体状态时，这些化合物显示出显着的稳定性在空气中，并在升高的温度下，与CLO ₄^-在90℃下在空气中被加热过夜后盐尚存。MEEPT-X与X的稳定性的不同趋势突出了浓度和环境对整体稳定性的重要性。

更新日期：2020-02-21

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