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首页> 外文期刊>Chemistry: A European journal >Functional carbo-Butadienes: Nonaromatic Conjugation Effects through a 14-Carbon, 24-π-Electron Backbone
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Functional carbo-Butadienes: Nonaromatic Conjugation Effects through a 14-Carbon, 24-π-Electron Backbone

机译：功能碳-丁二烯：通过14碳，24-π电子主链的非芳香族共轭作用

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摘要

A systematic study of carbo-butadiene motifs not embedded in an aromatic carbo-benzene ring is described. Dibutatrienylacetylene (DBA) targets R1-C(R)=C=C=C(Ph)- C≡C-C(Ph)=C=C=C(R)-R~2 are devised, in which R is C≡CSiiPr_3 and R~1 and R~2 are R, H, or 4-X-C_6H_4, with the latter including three known representatives (X: H, NMe_2, or NH_2). The synthesis method is based on the SnCl_2-mediated reduction of pentaynediols prepared by early or late divergent strategies; the latter allows access to a OMe–NO_2 push–pull diaryl-DBA. If R~1 and R~2 are H, an over-reduced dialkynylbutatriene (DAB) with two allenyl caps was isolated instead of the unsubstituted DBA. If R~1=R~2=R, the tetraalkynyl-DBA target was obtained, along with an over-reduced DBA product with a 12-membered 1,2-alkylidene-1H_2,2H_2-carbo-cyclobutadiene ring. X-ray crystallography shows that all of the acyclic DBAs adopt a planar trans–transoid–trans configuration. The maximum UV/Vis absorption wavelength is found to vary consistently with the overall π-conjugation extent and, more intriguingly, with the π-donor character of the aryl X substituents, which varies consistently with the first (reversible) reduction potential and first (irreversible) oxidation peak, as determined by voltammetry.
机译：描述了未嵌入芳族碳苯环中的碳丁二烯基序的系统研究。设计了二丁三烯基乙炔（DBA）目标R1-C（R）= C = C = C（Ph）-C≡CC（Ph）= C = C = C（R）-R〜2，其中R为C≡CSiiPr_3 R-1和R-2是R，H或4-X-C_6H_4，后者包括三个已知的代表（X：H，NMe_2或NH_2）。该合成方法是基于通过早期或晚期发散策略制备的SnCl_2介导的戊炔二醇的还原。后者允许访问OMe–NO_2推挽二芳基DBA。如果R-1和R-2为H，则分离具有两个烯基帽的过度还原的二炔基三丁烯（DAB）而不是未取代的DBA。如果R〜1 ＝ R〜2 ＝ R，则得到四炔基-DBA靶，以及具有12元1,2-亚烷基-1H_2,2H_2-碳环丁二烯环的过度还原的DBA产物。 X射线晶体学表明，所有非环状DBA均采用平面反式-反式-反式-构型。发现最大的UV / Vis吸收波长随整体π共轭程度而变化，更有趣的是随着芳基X取代基的π供体特性变化，该特性随第一（可逆）还原电位和第一（可逆）还原电位一致变化。伏安法测定）。

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