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首页> 外文期刊>Chemistry: A European journal >Z-Shaped Pyrrolo[3,2-b]pyrroles and Their Transformation into -Expanded Indolo[3,2-b]indoles
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Z-Shaped Pyrrolo[3,2-b]pyrroles and Their Transformation into -Expanded Indolo[3,2-b]indoles

机译：Z形吡咯并[3,2-b]吡咯及其向吲哚[3,2-b]吲哚的转化

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摘要

Sterically hindered 1,4-dihydropyrrolo[3,2-b]pyrroles possessing ortho-(arylethynyl)phenyl substituents at positions-2 and -5 were efficiently synthesized through a sila-Sonogashira reaction. These unique Z-shaped dyes showed relatively strong fluorescence in solution. Detailed optimization revealed that, in the presence of InCl3, these alkynes readily undergo an intramolecular double cyclization to give hexacyclic products bearing an indolo[3,2-b]indole skeleton in remarkable yields. Steady-state UV-visible spectroscopy revealed that upon photoexcitation, the prepared Z-shaped alkynes undergo mostly radiative relaxation leading to high fluorescence quantum yields. In the case of 7,14-dihydrobenzo[g]benzo[6,7]indolo[3,2-b]indoles, we believe that the substantial planarization of geometry in the excited state, is the underlying reason for the observed large Stokes shifts. The presence of additional electron-withdrawing groups makes it possible to further alter the photophysical properties. The two-photon absorption cross-section values of both families of dyes were found to be modest and the nature of the excited state responsible for two-photon absorption appeared to be strongly affected by the presence of peripheral groups. Serendipitous synthesis of unusual double-Z-shaped alkyne by Sonogashira and Glaser coupling is also reported.
机译：通过sila-Sonogashira反应有效地合成了位阻在2位和-5位具有邻-（芳乙炔基）苯基取代基的1,4-二氢吡咯并[3,2-b]吡咯。这些独特的Z形染料在溶液中显示出较强的荧光。详细的优化结果表明，在存在InCl3的情况下，这些炔烃易于经历分子内双环化作用，从而以惊人的收率得到带有吲哚[3,2-b]吲哚骨架的六环产物。稳态紫外可见光谱显示，在光激发下，制备的Z形炔烃大部分会发生辐射弛豫，从而导致高荧光量子产率。在7,14-二氢苯并[g]苯并[6,7]吲哚[3,2-b]吲哚的情况下，我们认为在激发态下几何结构的充分平坦化是观察到较大斯托克斯的根本原因转变。另外的吸电子基团的存在使得可以进一步改变光物理性质。发现两个染料家族的双光子吸收横截面值是适度的，并且负责双光子吸收的激发态的性质似乎受到外围基团的存在的强烈影响。还报道了Sonogashira和Glaser偶合意外合成不寻常的双Z形炔烃。

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