{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T08:14:07Z","timestamp":1790237647755,"version":"4.1.0"},"reference-count":76,"publisher":"Wiley","issue":"25","license":[{"start":{"date-parts":[[2025,3,27]],"date-time":"2025-03-27T00:00:00Z","timestamp":1743033600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,3,27]],"date-time":"2025-03-27T00:00:00Z","timestamp":1743033600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["51773076"],"award-info":[{"award-number":["51773076"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Topological [2+2] cycloaddition is known to provide a convenient synthetic route for cyclobutane derivatives from favorably dispositioned dienes. In this study, new (2Z,4E)\u20102\u2010(2,4\u2010difluorophenyl)\u20105\u2010phenylpenta\u20102,4\u2010dienenitrile (\n                    <jats:bold>HDE<\/jats:bold>\n                    ), (2Z,4E)\u20102\u2010(2,4\u2010difluorophenyl)\u20105\u2010(p\u2010tolyl)penta\u20102,4\u2010dienenitrile (\n                    <jats:bold>MeDE<\/jats:bold>\n                    ), (2Z,4E)\u20105\u2010(4\u2010chlorophenyl)\u20102\u2010(2,4\u2010difluorophenyl)penta\u20102,4\u2010dienenitrile (\n                    <jats:bold>ClDE<\/jats:bold>\n                    ), (2Z,4E)\u20105\u2010(4\u2010bromophenyl)\u20102\u2010(2,4\u2010difluorophenyl)penta\u20102,4\u2010dienenitrile (\n                    <jats:bold>BrDE<\/jats:bold>\n                    ), (2Z,4E)\u20102\u2010(2,4\u2010difluorophenyl)\u20105\u2010(4\u2010methoxyphenyl) penta\u20102,4\u2010dienenitrile (\n                    <jats:bold>MeODE<\/jats:bold>\n                    ), and (2Z,4E)\u20102\u2010(2,4\u2010difluorophenyl)\u20105\u2010(4\u2010(dimethylamino)phenyl)penta\u20102,4\u2010dienenitrile (\n                    <jats:bold>MeNDE<\/jats:bold>\n                    ) were synthesized, and their reactivity and selectivity were investigated in relation to their molecular packing in the respective crystals.\n                    <jats:bold>HDE<\/jats:bold>\n                    and\n                    <jats:bold>MeDE<\/jats:bold>\n                    , with head\u2010to\u2010tail (HT) arrangement, yielded only one type of photodimer. On the contrary,\n                    <jats:bold>ClDE<\/jats:bold>\n                    and\n                    <jats:bold>BrDE<\/jats:bold>\n                    , with head\u2010to\u2010head (HH) packing, and where the \u201colefin pairs\n                    <jats:sub>\u03b1,\u03b2\u2010\u03b1,\u03b2<\/jats:sub>\n                    \u201d and \u201colefin pairs\n                    <jats:sub>\u03b3,\u03b4\u2010\u03b3,\u03b4<\/jats:sub>\n                    \u201d satisfy Schimdt's criteria, reacted to a mixture of photoproducts. Kinetics analysis suggests that the reaction rates of\n                    <jats:bold>HDE<\/jats:bold>\n                    and\n                    <jats:bold>MeDE<\/jats:bold>\n                    are higher than those of\n                    <jats:bold>ClDE<\/jats:bold>\n                    and\n                    <jats:bold>BrDE<\/jats:bold>\n                    . This observation may be due to the strong non\u2010covalent interactions between the potentially reactive olefin pairs as suggested by energy decomposition analysis. Furthermore, the reaction activation energies for photodimerization of the HT\u2010packed olefin pairs are indeed lower than those of the HH\u2010arranged ones. The HT packing of the diphenyldienes not only enhances the reactivity in the topological [2+2] cycloaddition but also contributes chemospecificity, regiospecifity, and stereospecificity, all of which are essential for the preparation of specific cyclobutanes derivatives based on photodimerization.\n                  <\/jats:p>","DOI":"10.1002\/chem.202500442","type":"journal-article","created":{"date-parts":[[2025,3,17]],"date-time":"2025-03-17T23:33:21Z","timestamp":1742254401000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Head\u2010to\u2010Tail Packing to Facilitate [2+2] Cycloaddition for Green Synthesis of Cyclobutane Derivatives in Specific Configuration"],"prefix":"10.1002","volume":"31","author":[{"given":"Xiqiao","family":"Yang","sequence":"first","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liuyang","family":"Jin","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jingbo","family":"Sun","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuan","family":"Yue","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kaiqi","family":"Ye","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng","family":"Liu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chao","family":"Chen","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liang","family":"Li","sequence":"additional","affiliation":[{"name":"Smart Materials Lab New York University Abu Dhabi  Abu Dhabi 129188 United Arab Emirates"},{"name":"Novel Materials Development Lab Sorbonne University Abu Dhabi  Abu Dhabi 38044 United Arab Emirates"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pan\u010de","family":"Naumov","sequence":"additional","affiliation":[{"name":"Smart Materials Lab New York University Abu Dhabi  Abu Dhabi 129188 United Arab Emirates"},{"name":"Center for Smart Engineering Materials New York University Abu Dhabi  Abu Dhabi 129188 United Arab Emirates"},{"name":"Research Center for Environment and Materials Macedonian Academy of Sciences and Arts  Boulevard Krste Misirkov 2, MK\u20121000 Skopje Macedonia"},{"name":"Department of Chemistry, Molecular Design Institute New York University  100 Washington Square East New York New York 10003 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0486-532X","authenticated-orcid":false,"given":"Ran","family":"Lu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Supramolecular Structure and Materials, College of Chemistry Jilin University  Changchun 130021 P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,3,27]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CS00840K"},{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00040"},{"key":"e_1_2_7_1_3","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202301525"},{"key":"e_1_2_7_1_4","doi-asserted-by":"publisher","DOI":"10.1002\/zaac.19191050109"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c09285"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.187701002242"},{"key":"e_1_2_7_2_3","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00723"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2NP00034B"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-016-0233-1"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201403454"},{"key":"e_1_2_7_3_4","doi-asserted-by":"publisher","DOI":"10.1021\/ja054872i"},{"key":"e_1_2_7_3_5","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2020.1752207"},{"key":"e_1_2_7_3_6","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2005.04.007"},{"key":"e_1_2_7_3_7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01276"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac197127040647"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9640002000"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c00978"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202204141"},{"key":"e_1_2_7_5_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202304722"},{"key":"e_1_2_7_5_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202206249"},{"key":"e_1_2_7_5_5","author":"Juneja N.","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"e_1_2_7_5_6","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c07453"},{"key":"e_1_2_7_5_7","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.3c01014"},{"key":"e_1_2_7_5_8","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202401564"},{"key":"e_1_2_7_5_9","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS01050C"},{"key":"e_1_2_7_5_10","doi-asserted-by":"publisher","DOI":"10.1021\/accountsmr.4c00325"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)01209-Z"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(95)01210-9"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja001239i"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352713"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja974072a"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201705325"},{"key":"e_1_2_7_9_3","doi-asserted-by":"publisher","DOI":"10.1039\/D1CE00086A"},{"key":"e_1_2_7_9_4","doi-asserted-by":"publisher","DOI":"10.1039\/D3TC03060A"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09577"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-30597-w"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-42604-9"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/cg060643b"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c00833"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsapm.3c00291"},{"key":"e_1_2_7_13_3","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c04010"},{"key":"e_1_2_7_13_4","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC06732C"},{"key":"e_1_2_7_13_5","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC04053G"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.31635\/ccschem.020.202000350"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2TC02667H"},{"key":"e_1_2_7_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202203178"},{"key":"e_1_2_7_14_4","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202320223"},{"key":"e_1_2_7_14_5","doi-asserted-by":"publisher","DOI":"10.1039\/C7TA11139H"},{"key":"e_1_2_7_14_6","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-32894-w"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.2c00930"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.4c01033"},{"key":"e_1_2_7_15_3","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-29959-1"},{"key":"e_1_2_7_16_1","doi-asserted-by":"crossref","unstructured":"Cambridge Crystallographic Data Centre Supplementary crystallographic data for this paper are available free of charge from the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe. These data include 2269380 (forHDE) 2269417 (forMeDE) 2269418 (forClDE) 2269379 (forBrDE) 2269378 (forMeODE) 2269416 (forMeNDE) 2269421 (forD\u2010HDE) and 2269422 (forD\u2010MeDE) and can be accessed via the Access Structures service or directly athttps:\/\/www.ccdc.cam.ac.uk\/services\/structures?id=https:\/\/doi.org\/10.1002\/chem.202500442.","DOI":"10.1002\/chem.202500442"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.3c00965"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/D4CS00325J"},{"key":"e_1_2_7_17_3","doi-asserted-by":"publisher","DOI":"10.1039\/D3TC03586G"},{"key":"e_1_2_7_17_4","doi-asserted-by":"publisher","DOI":"10.1002\/smll.202307756"},{"key":"e_1_2_7_17_5","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b13364"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.1750380"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11661-010-0421-1"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC03060E"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja900803d"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/B713586F"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0108270187092783"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.3c00075"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4SC05723F"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1063\/5.0006002"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00031a008"},{"key":"e_1_2_7_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.22885"},{"key":"e_1_2_7_24_1","volume-title":"Gaussian 16, Revision B.01","author":"Frisch M. J.","year":"2016"},{"key":"e_1_2_7_25_1","doi-asserted-by":"crossref","unstructured":"a)G. K.Kole A.Chanthapally G. K.Tan J. J.Vittal Cryst. Growth Des.2015 15 5555;","DOI":"10.1021\/acs.cgd.5b01213"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3126849"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC05549J"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00398"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576719014092"},{"key":"e_1_2_7_28_2","first-page":"446","volume":"22","author":"Donnay J. D. H.","year":"1937","journal-title":"Am. Mineral."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202500442","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202500442","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202500442","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,1,28]],"date-time":"2026-01-28T08:48:16Z","timestamp":1769590096000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202500442"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,27]]},"references-count":76,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2025,5]]}},"alternative-id":["10.1002\/chem.202500442"],"URL":"https:\/\/doi.org\/10.1002\/chem.202500442","archive":["Portico"],"relation":{"has-preprint":[{"id-type":"doi","id":"10.22541\/au.173770396.67178180\/v1","asserted-by":"object"}]},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3,27]]},"assertion":[{"value":"2025-02-04","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-03-17","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-03-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500442"}}