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首页> 外文期刊>Chemistry: A European journal >A general method for constructing optically active supramolecular assemblies from intrinsically achiral water-insoluble free-base porphyrins
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A general method for constructing optically active supramolecular assemblies from intrinsically achiral water-insoluble free-base porphyrins

机译：由固有的非手性水不溶性游离碱卟啉构建旋光性超分子组装体的一般方法

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摘要

We have developed a general method to construct optically active porphyrin supramolecular assemblies by using a simple air-water interfacial assembly process. The method involved the in situ diprotonation of the free-base porphyrins at the air-water interface and subsequent assembly under compression. We showed that two intrinsically achiral water-insoluble free-base porphyrin derivatives, 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine (H2OEP) and 5,10,15,20-tetra-p-tolyl-21 H,23H-porphine (H2TPPMe), could be diprotonated when spread onto a 2.4 M hydrochloric acid solution surface, and the Langmuir-Schaefer (LS) films fabricated from the subphase exhibited strong circular dichroism (CD) absorption, whereas those fabricated from pure Milli-Q water subphase did not. The experimental data suggested that the helical stacking of the achiral porphyrin building blocks was responsible for the supramolecular chirality of the assemblies. Interestingly, such a method was successfully applied to a series of other intrinsically achiral free-base porphyrins such as 5,10,15,20-tetrakis(4-methoxyphenyl)-21 H,23H-porphine (H2TPPOMe), 5,10,15,20-tetraphenyl-21H,23H-porphine (H2TPP), 5,10,15,20-tetrakis(4-(allyloxy)phenyl)-21H,23H-porphine (H(2)TPPOA), and 5,10,1.5,20-tetrakis(3,5-dimethoxyphenyl)-21H,23H-porphine (H2TPPDOMe). A possible mechanism has been proposed. The method provides a facile way to obtain optically active porphyrin supramolecular assemblies by using intrinsically achiral water-insoluble free-base porphyrin derivatives.
机译：我们已经开发出一种通用的方法，可以通过使用简单的空气-水界面组装工艺来构建旋光性卟啉超分子组装体。该方法涉及在空气-水界面处的游离碱卟啉的原位双质子化，然后在压缩下组装。我们显示了两种固有的非手性水不溶性游离碱卟啉衍生物：2,3,7,8,12,13,17,18-八乙基-21H，23H-吗啡（H2OEP）和5,10,15,20-四对甲苯基21 H，23H-卟啉（H2TPPMe）散布到2.4 M盐酸溶液表面时可能会被双质子化，由该亚相制备的Langmuir-Schaefer（LS）膜表现出强圆二色性（CD）吸收，而由纯Milli-Q水子相制造的则没有。实验数据表明，非手性卟啉构件的螺旋堆积是组装体超分子手性的原因。有趣的是，这种方法已成功应用于一系列其他非手性的游离碱卟啉，例如5,10,15,20-四（4-甲氧基苯基）-21 H，23H-吗啡（H2TPPOMe），5,10， 15,20-四苯基-21H，23H-卟啉（H2TPP），5,10,15,20-四（4-（烯丙氧基）苯基）-21H，23H-卟啉（H（2）TPPOA）和5,10 ，1.5，20-四（3，5-二甲氧基苯基）-21H，23H-吗啡（H2TPPDOMe）。已经提出了一种可能的机制。该方法提供了一种通过使用固有的非手性水不溶性游离碱卟啉衍生物来获得旋光性卟啉超分子组装体的简便方法。

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