412304-80-4Relevant academic research and scientific papers
Nucleophilic conjugate 1,3-addition of phosphines to oligoynoates
Deng, Jie-Cheng,Kuo, Chih-Wei,Chuang, Shih-Ching
, p. 10580 - 10583 (2014)
Herein we have elucidated unusual and unique nucleophilic conjugate 1,3-addition reactions of surveyed oligoynoates toward phosphines through spectroscopic and single crystal X-ray diffraction analyses of three-component reaction products of oligoynoates, phosphines and aldehydes. This journal is the Partner Organisations 2014.
Light-induced Ligation of o-Quinodimethanes with Gated Fluorescence Self-reporting
Feist, Florian,Rodrigues, Leona L.,Walden, Sarah L.,Krappitz, Tim W.,Dargaville, Tim R.,Weil, Tanja,Goldmann, Anja S.,Blinco, James P.,Barner-Kowollik, Christopher
supporting information, p. 7744 - 7748 (2020/05/22)
We introduce a highly efficient photoligation system, affording a pro-fluorescent Diels-Alder product that, on demand, converts into an intensively fluorescent naphthalene via E1 elimination in the presence of catalytic amounts of acid. The Diels-Alder reaction of the photocaged diene (o-quinodimethane ether or thioether) with electron-deficient alkynes is induced by UV or visible light. In contrast to previously reported ligation techniques directly leading to fluorescent products, the fluorescence is turned on after the photoligation. Thus, the light absorption of the fluorophore does not undermine the photoligation via competitive absorption, and as a result, photobleaching or side reactions of the fluorophore are not observed. Critically, the gated generation of a fluorescent product allows for fluorometric determination of the conversion. We employ a simple synthesis strategy for heterobifunctional electron-deficient alkynes allowing for facile functionalization of payload molecules.
