One-Pot Access to Push-Pull Oligoenes by Sequential [2+2] Cycloaddition-Retroelectrocyclization Reactions

被引：27

作者：

Jayamurugan, Govindasamy ^{[1
]}

Finke, Aaron D. ^{[1
]}

Gisselbrecht, Jean-Paul ^{[2
]}

Boudon, Corinne ^{[2
]}

Schweizer, W. Bernd ^{[1
]}

Diederich, Francois ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, HCI, CH-8092 Zurich, Switzerland

[2] Univ Strasbourg, CNRS, Inst Chim UMR 7177, Lab Electrochim & Chim Phys Corps Solide, F-67081 Strasbourg, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 01期

关键词：

CHROMOPHORES; CHEMISTRY; POLYACETYLENE; RUTHENIUM; EFFICIENT; PI;

D O I：

10.1021/jo402440m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formal [2 + 2] cycloaddition-retroelectrocyclization reaction was employed as the key transformation to obtain donor-substituted, pi-conjugated polycyanohexa-1,3,5-trienes (TCHTs and PCHTs) and polycyanoocta-1,3,5,7-tetraenes from donor-substituted tetracyanobuta-1,3-dienes (TCBDs) and electron-rich alkynes. These push-pull-substituted oligoene chromophores were also accessed in good yield from tetracyanoethylene and donor-substituted alkynes by using a one-pot protocol. All bis-(N,N-dialkylanilino) donor-substituted push-pull trienes and tetraenes showed better electron-accepting potency and lower HOMO-LUMO gaps than the corresponding TCBDs, as evidenced by optical and electrochemical studies.

引用

页码：426 / 431

页数：6

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