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首页> 外文期刊>Chemistry: A European journal >Synthesis, characterization, and properties of subporphyrazines: A new class of nonplanar, aromatic macrocycles with absorption in the green region
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Synthesis, characterization, and properties of subporphyrazines: A new class of nonplanar, aromatic macrocycles with absorption in the green region

机译：亚卟啉的合成，表征和性质：在绿色区域吸收的一类新的非平面芳香大环化合物

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摘要

Novel subphthalocyanine analogues that display strong absorption in the green region have been synthesized by using a boron template cyclotrimerization of maleonitrile derivatives. The spectroscopic properties of these macrocycles indicate that, like subphthalocyanines, they have 14 a electrons and are aromatic compounds with a conical shape. The removal of the three fused benzene rings from the subphthalocyanine skeleton produces a 75-80 nm blue shift of the Q-band and a slight lowering of the absorption coefficients for this band. In addition, the reduction of the pi system from 18 to 14 electrons that accompanies progression from porphyrazines to subporphyrazines causes a hypsochromic shift of the Q-band of around 100 nm. Subporphyrazines that are peripherally functionalized with six thioether chains, and in which the sulfur atoms are attached directly to the pyrrole moieties, exhibit optical features that may be explained in terms of the extension of pi conjugation over the six thiolene groups, as well as strong pi donation from the sulfur lone pairs to the macrocycle. These two effects are quantitatively and qualitatively very similar to those observed for porphyrazines that possess the same type of substitution. In addition, the mesomorphic behavior at low temperatures of a macrocycle that is substituted with six thiododecyl chains was demonstrated by using differential scanning calorimetry and optical polarising microscopy.
机译：通过使用马来腈衍生物的硼模板环三聚合成了在绿色区域显示强吸收的新型亚酞菁类似物。这些大环的光谱性质表明，与亚酞菁一样，它们具有14 a电子，并且是具有圆锥形状的芳族化合物。从亚酞菁骨架上除去三个稠合苯环会产生Q波段75-80 nm的蓝移，并且该波段的吸收系数略有降低。另外，伴随着从卟啉向亚卟啉的发展，π系统从18个电子减少到14个电子，导致Q带的变色移动约为100nm。外围有六个硫醚链官能化且硫原子直接连接到吡咯部分上的亚卟啉类化合物显示的光学特征可通过pi共轭在六个硫烯基上的扩展以及强大的pi来解释从硫孤对到大环的捐赠。这两种作用在数量和质量上都与具有相同取代类型的卟啉嗪所观察到的相似。此外，通过使用差示扫描量热法和光学偏振显微镜证明了被六个硫十二烷基链取代的大环在低温下的介晶行为。

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