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Synthesis, Structural Characterization, and Photochemical [2 + 2] Cycloaddition of a Coordination Polymer: Multiweek Inorganic-Organic Chemistry Experiments

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Title: Synthesis, Structural Characterization, and Photochemical [2 + 2] Cycloaddition of a Coordination Polymer: Multiweek Inorganic-Organic Chemistry Experiments
Language: English
Authors: Yu-Xuan Hong, Meng-Fan Wang, Yu Ge, Hong Yu, Chun-Yan Ni, Wei-Yi Chen, Pierre Braunstein (ORCID 0000-0002-4377-604X), Jian-Ping Lang (ORCID 0000-0003-2942-7385)
Source: Journal of Chemical Education. 2023 100(11):4430-4437.
Availability: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Peer Reviewed: Y
Page Count: 8
Publication Date: 2023
Document Type: Journal Articles
Reports - Research
Education Level: Higher Education
Postsecondary Education
Descriptors: Science Experiments, Organic Chemistry, Scientific Concepts, Undergraduate Study, College Science, Skill Development, Laboratory Experiments, Thinking Skills, Student Research, Research Skills, Experiential Learning
DOI: 10.1021/acs.jchemed.3c00386
ISSN: 0021-9584
1938-1328
Abstract: The [2 + 2] photocycloaddition reaction of olefins is an effective, atom-economical approach to produce cyclobutane compounds in organic synthetic chemistry, and they usually exhibit high regioselectivity and stereoselectivity. Here we devised a solid-state [2 + 2] photocycloaddition experiment that introduces senior undergraduate students with the principles of coordination chemistry, organic chemistry, structural chemistry, and supramolecular chemistry, which have been widely used in material chemistry, catalysis, nanotechnology, and other fields. The experiment employs coordination interactions that act as templates to directing the [2 + 2] photocycloaddition reaction. A photoreactive coordination polymer [Zn­(oba)­(4-npy)][subscript 2]·(4-npy)[subscript 0.25] (1, 4-npy = (E)-4-(2-(naphthalen-1-yl)­vinyl)­pyridine,H[subscript 2]oba = 4,4'-oxidibenzoic acid) is solvothermally prepared and undergoes a [2 + 2] photocycloaddition reaction, affording the new compound [Zn[subscript 2](oba)[subscript 2](HT-pncb)]­(4-npy)[subscript 0.25] (1a, HT-pncb = "rctt"-1,3-bis­(4-pyridyl)-2,4-bis­(1-naphthyl) ­cyclobutane; HT = head-to-tail) upon UV light illumination. The experiments will strengthen the students' experimental skills while the diverse characterization experiments will allow them to experience the contribution of each method and their complementarity in monitoring the structural changes that occur upon photoreaction. This comprehensive project will help students broaden the research horizon, cultivate research skills, follow strict scientific procedures, and promote rigorous thinking in a laboratory course.
Abstractor: As Provided
Entry Date: 2024
Accession Number: EJ1445371
Database: ERIC
FullText Text:
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PubType: Academic Journal
PubTypeId: academicJournal
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IllustrationInfo
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  Data: Synthesis, Structural Characterization, and Photochemical [2 + 2] Cycloaddition of a Coordination Polymer: Multiweek Inorganic-Organic Chemistry Experiments
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  Data: <searchLink fieldCode="AR" term="%22Yu-Xuan+Hong%22">Yu-Xuan Hong</searchLink><br /><searchLink fieldCode="AR" term="%22Meng-Fan+Wang%22">Meng-Fan Wang</searchLink><br /><searchLink fieldCode="AR" term="%22Yu+Ge%22">Yu Ge</searchLink><br /><searchLink fieldCode="AR" term="%22Hong+Yu%22">Hong Yu</searchLink><br /><searchLink fieldCode="AR" term="%22Chun-Yan+Ni%22">Chun-Yan Ni</searchLink><br /><searchLink fieldCode="AR" term="%22Wei-Yi+Chen%22">Wei-Yi Chen</searchLink><br /><searchLink fieldCode="AR" term="%22Pierre+Braunstein%22">Pierre Braunstein</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0002-4377-604X">0000-0002-4377-604X</externalLink>)<br /><searchLink fieldCode="AR" term="%22Jian-Ping+Lang%22">Jian-Ping Lang</searchLink> (ORCID <externalLink term="https://orcid.org/0000-0003-2942-7385">0000-0003-2942-7385</externalLink>)
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  Data: <searchLink fieldCode="SO" term="%22Journal+of+Chemical+Education%22"><i>Journal of Chemical Education</i></searchLink>. 2023 100(11):4430-4437.
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  Data: Division of Chemical Education, Inc. and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
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  Data: 10.1021/acs.jchemed.3c00386
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  Data: 0021-9584<br />1938-1328
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  Data: The [2 + 2] photocycloaddition reaction of olefins is an effective, atom-economical approach to produce cyclobutane compounds in organic synthetic chemistry, and they usually exhibit high regioselectivity and stereoselectivity. Here we devised a solid-state [2 + 2] photocycloaddition experiment that introduces senior undergraduate students with the principles of coordination chemistry, organic chemistry, structural chemistry, and supramolecular chemistry, which have been widely used in material chemistry, catalysis, nanotechnology, and other fields. The experiment employs coordination interactions that act as templates to directing the [2 + 2] photocycloaddition reaction. A photoreactive coordination polymer [Zn­(oba)­(4-npy)][subscript 2]·(4-npy)[subscript 0.25] (1, 4-npy = (E)-4-(2-(naphthalen-1-yl)­vinyl)­pyridine,H[subscript 2]oba = 4,4'-oxidibenzoic acid) is solvothermally prepared and undergoes a [2 + 2] photocycloaddition reaction, affording the new compound [Zn[subscript 2](oba)[subscript 2](HT-pncb)]­(4-npy)[subscript 0.25] (1a, HT-pncb = "rctt"-1,3-bis­(4-pyridyl)-2,4-bis­(1-naphthyl) ­cyclobutane; HT = head-to-tail) upon UV light illumination. The experiments will strengthen the students' experimental skills while the diverse characterization experiments will allow them to experience the contribution of each method and their complementarity in monitoring the structural changes that occur upon photoreaction. This comprehensive project will help students broaden the research horizon, cultivate research skills, follow strict scientific procedures, and promote rigorous thinking in a laboratory course.
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        Value: 10.1021/acs.jchemed.3c00386
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      – Text: English
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    Subjects:
      – SubjectFull: Science Experiments
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      – SubjectFull: Organic Chemistry
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      – TitleFull: Synthesis, Structural Characterization, and Photochemical [2 + 2] Cycloaddition of a Coordination Polymer: Multiweek Inorganic-Organic Chemistry Experiments
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