Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
Org Lett. 2011 May 6;13(9):2380-3. doi: 10.1021/ol2006264. Epub 2011 Apr 1.
Alkyl-Grignard addition to meso-tetraphenylporpholactone generates monoalkyl- and gem-bis-alkyloxazolochlorins. Together with compounds made by further synthetic manipulations of these derivatives, a series of chlorin-type chromophores with modulated optical properties is generated. Furthermore, their OsO(4)-mediated dihydroxylations and subsequent functional group transformations generate a family of bacteriochlorins that possess substituent-dependent optical properties. Thus, the formal replacement of a pyrrolidine moiety in chlorins and bacteriochlorins by variously substituted oxazoles is a flexible methodology to generate novel and stable chromophores that are tunable over a considerable range of the optical spectrum.
烷基-格氏试剂加成到中四苯基卟啉内酯生成单烷基-和偕二烷基-氧杂唑氯代卟啉。通过对这些衍生物的进一步合成操作，生成了一系列具有调制光学性质的氯代卟啉类发色团。此外，它们的 OsO(4)介导的二羟基化和随后的官能团转化生成了一系列具有取代基依赖性光学性质的细菌叶绿素。因此，通过各种取代的恶唑取代卟啉和细菌叶绿素中的吡咯烷部分是一种灵活的方法，可以生成具有相当宽的光学光谱可调性的新型稳定发色团。
