Towards the synthesis of insulated oligoynes: A ring-closing-metathesis approach to molecular encapsulation |
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| Institution: | 1. Tarragona, Spain;2. Riverside, CA, USA;1. School of Materials Science and Engineering, Tianjin University of Technology, Tianjin 300384, PR China;2. Department of Chemistry, Durham University, Durham DH1 3LE, UK;1. MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, & State Key Lab of Silicon Materials, Zhejiang University, Hangzhou 310027, PR China;2. Department of Chemistry and Bioscience, Aalborg University, Fredrik Bajers Vej 7H, DK-9220, Aalborg East, Aalborg, Denmark;3. Sino-Danish Centre for Education and Research (SDC), Niels Jensens Vej 2, DK-8000 Aarhus, Denmark;4. Department of Energy Conversion and Storage, Technical University of Denmark, Frederiksborgvej 399, DK-4000 Roskilde, Denmark;1. Universidade Federal de Santa Catarina – UFSC, Centro Tecnológico – CTC, Departamento de Engenharia Civil, Campus Reitor João David Ferreira Lima, Rua João Pio Duarte da Silva, 205, Bairro Córrego Grande, Florianópolis, Santa Catarina CEP 88037-000, Brazil;2. Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada;1. Network of Institutes for Solar Energy (CSIR-NISE), Inorganic & Physical Chemistry Division, CSIR – Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500607, India;2. R & D Center for Science and Engineering, JEC Group of Colleges, Jaipur Engineering College Campus, Kukas, Jaipur 303101, India;1. Department of Physics and Astronomy, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1, Canada;2. Department of General Sciences, Prince Sultan University, Rafha Street, P. O. Box 66833, Riyadh 11586, Saudi Arabia;3. Department of Chemical Engineering, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1, Canada;4. Department of Mechanical, Aerospace and Biomedical Engineering, University of Tennessee Knoxville, 1512 Middle Drive, Knoxville, TN 37996, USA;1. Department of Chemistry and Biochemistry, South Dakota State University, Brookings, South Dakota 57007, United States;2. Center for Materials Research, Norfolk State University, Norfolk, VA 23504, United States |
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| Abstract: | Masked hexayne 18 was prepared in 11 steps from commercially available reagents. The four butenyl substituents contained within the two arylsilane residues in 18 have been used in a double ring-closing-metathesis operation in an attempt to encapsulate the π-conjugated framework. When 18 was treated with Grubbs’ 1st generation metathesis catalyst however, double ring-closing metathesis provided macrocycle 19 as the major product in good yield. Reasons why the macrocycle in 19 crowns, rather than encapsulates, the π-conjugated framework are discussed. |
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