Palladium-catalyzed cycloisomerizations of diarylacetylenes: Synthesis, structures, and physical properties of highly substituted naphthalenes and 8,8 a-dihydrocyclopenta[a]indenes

Wu T.-C.; Tai C.-C.; Tiao H.-C.; Chang Y.-T.; Liu C.-C.; Li C.-H.; Huang C.-H.; Kuo M.-Y.; Wu Y.-T.

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Palladium-catalyzed cycloisomerizations of diarylacetylenes: Synthesis, structures, and physical properties of highly substituted naphthalenes and 8,8 a-dihydrocyclopenta[a]indenes

机译：钯催化的二芳基乙炔的环异构化：高度取代的萘和8,8 a-二氢环戊[a]茚的合成，结构和物理性质

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Depending on the electronic properties of their substituents, the major products generated by palladium-catalyzed cycloisomerizations of diarylalkynes are either highly substituted 8,8a-dihydrocyclopenta[a]indenes 3 or naphthalenes 4. The structures of these compounds were verified by X-ray crystallographic analysis. Many functional groups tolerated the reaction conditions evaluated in this study. The isotope-labeled experiments indicated that added water has a critical role in forming both classes of compounds. The photophysical and electrochemical properties of cycloadducts 3 and their analogues were systematically studied and compared with computational predictions based on density functional theory. Dihydrocyclopenta[a]indenes 3 in either solid or liquid form display strong luminescence, whereas cyclopenta[a]indene 11 j is practically nonfluorescent. The functional groups directly attached to the backbone of compound 3 significantly influenced physical properties. The steric effect arising from the aryl substituents caused different luminescence phenomena, including aggregation-induced and -enhanced emission.

机译：取决于其取代基的电子性质，二芳基炔烃的钯催化环异构化反应生成的主要产物是高度取代的8,8a-二氢环戊[a]茚3或萘4。这些化合物的结构已通过X射线晶体学验证分析。许多官能团耐受本研究中评估的反应条件。同位素标记的实验表明，加水在形成这两类化合物中都起着至关重要的作用。系统研究了环加合物3及其类似物的光物理和电化学性质，并将其与基于密度泛函理论的计算预测进行了比较。固态或液态的二氢环戊[a]茚3均显示强发光，而环戊[a]茚11j实际上是非荧光的。直接连接到化合物3的骨架上的官能团会显着影响物理性质。由芳基取代基引起的空间效应引起不同的发光现象，包括聚集诱导的和增强的发射。

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《Chemistry: A European journal》 |2011年第26期|共8页
作者
Wu T.-C.; Tai C.-C.; Tiao H.-C.; Chang Y.-T.; Liu C.-C.; Li C.-H.; Huang C.-H.; Kuo M.-Y.; Wu Y.-T.;
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正文语种 eng
中图分类应用化学;
关键词
aggregation; alkynes; cycloisomerization; naphthalene; palladium;

机译：聚集;炔烃;环异构化;萘;钯;

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1. Palladium-catalyzed cycloisomerizations of diarylacetylenes: Synthesis, structures, and physical properties of highly substituted naphthalenes and 8,8 a-dihydrocyclopenta[a]indenes [J] . Wu T.-C., Tai C.-C., Tiao H.-C., Chemistry: A European journal . 2011,第26期

机译：钯催化的二芳基乙炔的环异构化：高度取代的萘和8,8 a-二氢环戊[a]茚的合成，结构和物理性质
2. Palladium-Catalyzed Cycloisomerizations of Diarylacetylenes: Synthesis, Structures, and Physical Properties of Highly Substituted Naphthalenes and 8,8?a-Dihydrocyclopenta[a]indenes? [J] . Tsun-Cheng Wu, Dr. Chia-Cheng Tai, Hsin-Chieh Tiao, Chemistry - A European Journal . 2011,第26期

机译：钯催化的二芳基乙炔的环异构化：高度取代的萘和8,8-α-二氢环戊[a]茚的合成，结构和物理性质？
3. Synthesis,Structure,and Photophysical Properties of Highly Substituted 8,8a-Dihydrocydopenta[a]indenes [J] . Yao-Ting Wu, Ming-Yu Kuo, Yu-Ting Chang Angewandte Chemie . 2008,第51期

机译：高度取代的8,8a-二氢环戊二烯[a]茚的合成，结构和光物理性质
4. Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives [C] . J. Starch, J. Sykora, J. Cermak European Symposium on Organic Chemistry . 2009

机译：通过联苯甲萘衍生物的环晶体化合成六氢和1-甲氧基甲丙烯
5. I. Synthesis of substituted naphthalenes utilizing active nickel. II. Synthesis of substituted naphthoquinones and formation of a charge transfer complex. III. Synthesis of substituted 1,4-diphenyl-2-butenes from (eta(6):eta(6)-1,4-diphenyl-1,3-butadiene)-bis(tricarbonylchromium) [D] . Forkner, Matthew W. 1988

机译：I.利用活性镍合成取代的萘。二。取代萘醌的合成和电荷转移配合物的形成。三，由（eta（6）：eta（6）-1,4-二苯基-1,3-丁二烯）-双（三羰基铬）合成取代的1,4-二苯基-2-丁烯
6. Two Palladium-Catalyzed Domino Reactions from One Set of Substrates/Reagents: Efficient Synthesis of Substituted Indenes and cis-Stilbenoid Hydrocarbons from the Same Internal Alkynes and Hindered Grignard Reagents [O] . Cheng-Guo Dong, Pik Yeung, Qiao-Sheng Hu -1

机译：从一组底物/试剂中进行两个钯催化的多米诺反应：从相同的内部炔烃和受阻的格氏试剂中高效合成取代的茚类和顺式-类苯乙烯烃
7. Synthesis of aryl substituted indanones and indenes via a highly efficient ligand-free palladium-catalyzed Suzuki coupling process [O] . Yuming Song, Yamei Xie, Minjian Chen, 2016

机译：通过高效无配体的钯催化的suzuki偶联方法合成芳基取代的茚满酮和茚
8. Soluble, Highly Conjugated Derivatives of Polyacetylene from the Ring-OpeningMetathesis Polmerization of Monosubstituted Cyclooctatetraenes: Synthesis and the Relationship Between Polymer Structure and Physical Properties [R] . Gorman, C. B., Ginsburg, E. J., Grubbs, R. H. 1993

机译：可溶性高共轭衍生物的聚乙炔来自单取代环辛四烯的开环复合聚合：合成及其与聚合物结构和物理性质的关系

Palladium-catalyzed cycloisomerizations of diarylacetylenes: Synthesis, structures, and physical properties of highly substituted naphthalenes and 8,8 a-dihydrocyclopenta[a]indenes

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