Synthesis and Self‐Aggregation of Chlorophyll‐a Derivatives with Ethynylene and Phenylene Groups Inserted Between the Hydroxymethyl Group and the Chlorin π‐Skeleton,ChemPhotoChem

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Synthesis and Self‐Aggregation of Chlorophyll‐a Derivatives with Ethynylene and Phenylene Groups Inserted Between the Hydroxymethyl Group and the Chlorin π‐Skeleton
ChemPhotoChem ( IF 3.0 ) Pub Date : 2020-02-14 , DOI: 10.1002/cptc.202000012
Takeo Nakano ₁ , Hitoshi Tamiaki ₁

Affiliation

Chlorophyll(Chl)‐a derivatives containing some rigid linkers in the C3‐substituent, inserted between a hydroxymethyl group and a zinc 13¹‐oxo‐chlorin moiety, were synthesized as models of bacteriochlorophyll‐c/d/e molecules in the main light‐harvesting antennae (chlorosomes) of photosynthetic green bacteria. These model compounds were synthesized from a C3‐ethynylated Chl‐a derivative via several coupling reactions, and the lengths of the linkers were controlled by ethynylene and p‐phenylene groups. In less polar organic solvents or an aqueous micellar solution, some derivatives self‐aggregated in a J‐type fashion similar to that observed in natural chlorosomes, which was confirmed with UV/Vis absorption and CD spectroscopies. Their self‐aggregation abilities were dependent on the length of the inserted linkers and the conformation of the propargylic/benzylic alcoholic hydroxy groups.

中文翻译：

叶绿素a衍生物的合成和自聚集，亚乙基和亚苯基插入羟甲基和氯代π-骨架之间

叶绿素（Chl）-在C3-取代基中包含一些刚性连接基的衍生物，插入在羟甲基基团和13 ^1-氧代二氧合锌锌部分之间，是作为主要叶绿素c / d / e分子模型的合成收获光合作用绿色细菌的触角（绿体）。这些模型化合物从一个C3-乙炔Chl-合成一个衍生物经由几个偶联反应，和所述接头的长度是由亚乙炔基和受控的p亚苯基的基团。在极性较小的有机溶剂或胶束水溶液中，某些衍生物会在J分子中自聚集这种类型的方式类似于在天然脂质体中观察到的方式，这已通过UV / Vis吸收和CD光谱学证实。它们的自聚集能力取决于所插入接头的长度和炔丙基/苄基醇羟基的构象。

更新日期：2020-02-14

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