Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics.
Fluorinated porphyrinoids as efficient platforms for new photonic materials, sensors, and therapeutics.
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DOI：
10.1039/c5ob01839k
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发表时间：
2016-01-14
影响因子：
3.2
通讯作者：
Drain CM
中科院分区：
文献类型：
--
作者：
Bhupathiraju NVSDK;Rizvi W;Batteas JD;Drain CM
卟啉类化合物是一种强健的杂环染料，由于其可调的光物理性质、多种修饰周边的方法以及对大多数过渡金属的螯合能力，在医学和作为光子材料方面的应用得到了广泛的研究。商业应用包括用作光盘中的酞菁染料，光动力疗法中的卟啉，以及氧传感器。这些染料的大多数应用需要外环基团来改善溶解性，针对疾病，调制光物理性质，或者将自组织引导到具有所需光子性质的结构中。卟啉类化合物的合成依赖于所需的应用，但从头合成通常涉及几个步骤，耗时，并导致低分离产率。因此，可以快速有效地进行修饰以评估新的分子结构的核心类卟啉平台的应用使研究人员能够专注于设计概念而不是合成方法，并向更广泛的科学界开放了类卟啉化学。我们专注于几个广泛可用的、商业上可行的卟啉类化合物作为平台：Meso-全氟苯基卟啉、全氟苯基酞菁和Meso-全氟苯基珊瑚。全氟苯基卟啉很容易转化为氯、细菌氯和异细菌氯。所有六个核心平台的衍生物可以通过温和的亲核芳香取代反应，使用带有多种官能团的初级S、N和O亲核试剂进行有效和可控的合成。剩余的氟基团增强了染料的光稳定性和氧化稳定性，可以作为光谱信号来表征化合物或使用19F核磁共振进行成像应用。本文综述了氟化卟啉类化合物的化学，这些化合物被用作创建光活性化合物在医学和材料中的应用的平台。
Porphyrinoids are robust heterocyclic dyes studied extensively for their applications in medicine and as photonic materials because of their tunable photophysical properties, diverse means of modifying the periphery, and the ability to chelate most transition metals. Commercial applications include their use as phthalocyanine dyes in optical discs, porphyrins in photodynamic therapy, and as oxygen sensors. Most applications of these dyes require exocyclic moieties to improve solubility, target diseases, modulate photophysical properties, or direct the self-organization into architectures with desired photonic properties. The synthesis of the porphyrinoid depends on the desired application, but the de novo synthesis often involves several steps, is time consuming, and results in low isolated yields. Thus, the application of core porphyrinoid platforms that can be rapidly and efficiently modified to evaluate new molecular architectures allows researchers to focus on the design concepts rather than the synthesis methods, and opens porphyrinoid chemistry to a broader scientific community. We have focused on several widely available, commercially viable porphyrinoids as platforms: meso-perfluorophenylporphyrin, perfluoro-phthalocyanine, and meso-perfluorophenylcorrole. The perfluorophenylporphyrin is readily converted to the chlorin, bacteriochlorin, and isobacteriochlorin. Derivatives of all six of these core platforms can be efficiently and controllably made via mild nucleophilic aromatic substitution reactions using primary S, N, and O nucleophiles bearing a wide variety of functional groups. The remaining fluoro groups enhance the photo and oxidative stability of the dyes and can serve as spectroscopic signatures to characterize the compounds or in imaging applications using 19F NMR. This review provides an overview of the chemistry of fluorinated porphyrinoids that are being used as a platform to create libraries of photo-active compounds for applications in medicine and materials.
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影响因子：
19
作者：
Borisov, Sergey M.;Vasylevska, Anna S.;Wolfbeis, Otto S.
通讯作者：
Wolfbeis, Otto S.
影响因子：
5
作者：
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影响因子：
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作者：
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通讯作者：
Drain CM
影响因子：
2.3
作者：
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通讯作者：
Gonsalves, AMDR
影响因子：
1.8
作者：
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通讯作者：
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