{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T19:16:04Z","timestamp":1788290164711,"version":"build-2803163510"},"reference-count":51,"publisher":"American Chemical Society (ACS)","issue":"34","license":[{"start":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T00:00:00Z","timestamp":1787011200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T00:00:00Z","timestamp":1787011200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T00:00:00Z","timestamp":1787011200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","award":["25K01732"],"award-info":[{"award-number":["25K01732"]}],"id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>In this study, we used atmospheric-pressure droplet laser-ablation mass spectrometry to elucidate the chemical pathways induced by UV-laser irradiation of carbon tetrachloride (CCl4) droplets containing various alcohols. We focused on the reaction dynamics following the laser-induced generation of trichloromethyl radicals (CCl3) and ions (CCl3+) in the microdroplets. Mass spectrometric analysis revealed that CCl3+ initiated sequential substitution reactions. With phenol, sequential substitution occurred, resulting in the formation of mono-, di-, and trisubstituted ions. Conversely, methanol and ethanol exclusively yielded trisubstituted species [C(OR)3+], regardless of the concentration, which we attributed to the formation of alcohol aggregates in the CCl4 solution. For bulkier alcohols, steric hindrance suppressed substitution, and this favored CCl3-mediated hydrogen abstraction followed by radical coupling. Isotope-labeling experiments with ethanol revealed a higher abundance of coupling products derived from beta-site abstraction than from alpha-site abstraction, suggesting distinct kinetic preferences in the coupling step. These findings demonstrate that the microdroplet environment and molecular aggregation dictate the selectivity of laser-induced organic synthesis. This knowledge provides a basis for developing novel pulsed-laser-based synthetic methodologies.<\/jats:p>","DOI":"10.1021\/acs.jpca.6c02615","type":"journal-article","created":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T05:01:53Z","timestamp":1787029313000},"page":"6807-6814","source":"Crossref","is-referenced-by-count":0,"title":["Laser Organic Synthesis\nof Trichloromethyl Radicals\/Ions\nand Study of Subsequent Reactions by Droplet Mass Spectrometry"],"prefix":"10.1021","volume":"130","author":[{"given":"Yuki","family":"Anami","sequence":"first","affiliation":[{"name":"Gakushuin University , , 1-5-1 Mejiro , , ,","place":["Toshima\u2212ku, Tokyo, Japan, 171-8588"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takuma","family":"Tokuhara","sequence":"additional","affiliation":[{"name":"Gakushuin University , , 1-5-1 Mejiro , , ,","place":["Toshima\u2212ku, Tokyo, Japan, 171-8588"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenichi","family":"Okutsu","sequence":"additional","affiliation":[{"name":"Gakushuin University , , 1-5-1 Mejiro , , ,","place":["Toshima\u2212ku, Tokyo, Japan, 171-8588"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6239-9289","authenticated-orcid":true,"given":"Jun-ya","family":"Kohno","sequence":"additional","affiliation":[{"name":"Gakushuin University , , 1-5-1 Mejiro , , ,","place":["Toshima\u2212ku, Tokyo, Japan, 171-8588"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,18]]},"reference":[{"issue":"2","key":"2026090114375127800_cit1","doi-asserted-by":"publisher","first-page":"2752","DOI":"10.1021\/acs.chemrev.1c00332","article-title":"Technological\nInnovations in Photochemistry for Organic Synthesis: Flow Chemistry,\nHigh-Throughput Experimentation, Scale-up, and Photoelectrochemistry","volume":"122","author":"Buglioni","year":"2022","journal-title":"Chem. 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Phys."},{"issue":"3","key":"2026090114375127800_cit4","doi-asserted-by":"publisher","first-page":"177","DOI":"10.1155\/1990\/42676","article-title":"UV Multiphoton\nInduced Chemistry\nof Nitrobenzene in Solution","volume":"10","author":"Belbruno","year":"1990","journal-title":"Laser Chem."},{"issue":"12","key":"2026090114375127800_cit5","doi-asserted-by":"publisher","first-page":"8071","DOI":"10.1039\/C7CP08011E","article-title":"Mechanistic Insights\ninto Two-Photon-Driven Photocatalysis in Organic Synthesis","volume":"20","author":"Marchini","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"issue":"9","key":"2026090114375127800_cit6","doi-asserted-by":"publisher","first-page":"717","DOI":"10.1021\/ar000107r","article-title":"One- vs Two-Photon\nProcesses in the Photochemistry of 1, n -Dihaloalkanes","volume":"34","author":"Miranda","year":"2001","journal-title":"Acc. Chem. 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Jpn."},{"issue":"1\u20133","key":"2026090114375127800_cit20","doi-asserted-by":"publisher","first-page":"146","DOI":"10.1016\/j.cplett.2005.12.056","article-title":"Ion Formation to the Gas Phase by\nLaser Ablation on a Droplet Beam","volume":"420","author":"Kohno","year":"2006","journal-title":"Chem. Phys.\nLett."},{"issue":"34","key":"2026090114375127800_cit21","doi-asserted-by":"publisher","first-page":"7208","DOI":"10.1021\/acs.jpca.4c03597","article-title":"Hydrogen\/Deuterium\nExchange Reaction\nRate of Cytochrome c Determined by Droplet Collision Atmospheric Pressure\nInfrared Laser Ablation Mass Spectrometry","volume":"128","author":"Kawashima","year":"2024","journal-title":"J.\nPhys. Chem. 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Chem."},{"issue":"14","key":"2026090114375127800_cit25","doi-asserted-by":"publisher","first-page":"2053","DOI":"10.1021\/ja00897a005","article-title":"The Photolysis\nof Carbon Tetrachloride in the Presence\nof Ethane and Ethylene","volume":"85","author":"Roquitte","year":"1963","journal-title":"J. Am. Chem. Soc."},{"issue":"5","key":"2026090114375127800_cit26","doi-asserted-by":"publisher","first-page":"2925","DOI":"10.1063\/1.439491","article-title":"UV Laser Photochemistry of CCl4 and CCl3F","volume":"72","author":"Tiee","year":"1980","journal-title":"J. Chem. Phys."},{"issue":"6","key":"2026090114375127800_cit27","doi-asserted-by":"publisher","first-page":"627","DOI":"10.1007\/BF00534442","article-title":"Photochemical\nand Photocatalytic Reactions of Carbon Tetrachloride with Alcohols","volume":"25","author":"Kuchmii","year":"1989","journal-title":"Theor. Exp. Chem."},{"issue":"9","key":"2026090114375127800_cit28","doi-asserted-by":"publisher","first-page":"1435","DOI":"10.1139\/v73-216","article-title":"Photochemistry of\nKetones in Carbon Tetrachloride Solution","volume":"51","author":"Pavlik","year":"1973","journal-title":"Can.\nJ. Chem."},{"issue":"3","key":"2026090114375127800_cit29","doi-asserted-by":"publisher","first-page":"443","DOI":"10.1021\/ja01306a018","article-title":"The Photo-Oxidation of Liquid Carbon Tetrachloride","volume":"57","author":"Lyons","year":"1935","journal-title":"J. Am. Chem. Soc."},{"issue":"8","key":"2026090114375127800_cit30","doi-asserted-by":"publisher","first-page":"771","DOI":"10.1002\/kin.550130808","article-title":"The Kinetics of Radiation-induced\nHydrogen Abstraction\nby CCl3 Radicals in the Liquid Phase: Cyclohexene","volume":"13","author":"Alfassi","year":"1981","journal-title":"Int. J. Chem. Kinet."},{"issue":"19","key":"2026090114375127800_cit31","doi-asserted-by":"publisher","first-page":"4296","DOI":"10.1021\/jp051072l","article-title":"Recombination Dynamics\nand Hydrogen Abstraction Reactions of Chlorine Radicals in Solution","volume":"109","author":"Sheps","year":"2005","journal-title":"J. Phys. Chem. A"},{"issue":"23","key":"2026090114375127800_cit32","doi-asserted-by":"publisher","first-page":"5813","DOI":"10.1039\/b207529f","article-title":"Kinetics\nof Reactions of Chlorine Atoms with a Series of Alkenes at 1 Atm and\n298 K: Structure and Reactivity","volume":"4","author":"Ezell","year":"2002","journal-title":"Phys. Chem.\nChem. Phys."},{"issue":"5","key":"2026090114375127800_cit33","doi-asserted-by":"publisher","first-page":"926","DOI":"10.1021\/jp962021e","article-title":"Theoretical Studies of Hydrogen Abstraction\nfrom 2-Propanol by OH Radical","volume":"101","author":"Luo","year":"1997","journal-title":"J. Phys. Chem.\nA"},{"issue":"13","key":"2026090114375127800_cit34","doi-asserted-by":"publisher","first-page":"134503","DOI":"10.1063\/1.5021634","article-title":"Alkyl Hydrogen Atom Abstraction Reactions of the CN\nRadical with Ethanol","volume":"148","author":"Athokpam","year":"2018","journal-title":"J. Chem. Phys."},{"key":"2026090114375127800_cit35","doi-asserted-by":"publisher","first-page":"1350","DOI":"10.1126\/science.adl5890","article-title":"AlcoHol-alcoHol cross-coupling\nenabled by S H 2 radical sorting","volume":"383","author":"Chen","year":"2024","journal-title":"Science"},{"issue":"1","key":"2026090114375127800_cit36","doi-asserted-by":"publisher","first-page":"158","DOI":"10.1562\/2005-06-03-RA-563","article-title":"The Laser Two-Photon\nPhotolysis of Liquid Carbon Tetrachloride","volume":"82","author":"Zhang","year":"2006","journal-title":"Photochem.\nPhotobiol."},{"issue":"10","key":"2026090114375127800_cit37","doi-asserted-by":"publisher","first-page":"1839","DOI":"10.1007\/s13361-011-0193-x","article-title":"Gas Chromatographic-Ion Trap Mass\nSpectrometric Analysis of Volatile Organic Compounds by Ion\u2013Molecule\nReactions Using the Electron-Deficient Reagent Ion CCl3+","volume":"22","author":"Wang","year":"2011","journal-title":"J. Am. Soc. 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Sci."},{"issue":"50","key":"2026090114375127800_cit42","doi-asserted-by":"publisher","first-page":"15455","DOI":"10.1021\/ja037328n","article-title":"Kinetic and Thermodynamic\nBarriers to Carbon and Oxygen Alkylation of Phenol and Phenoxide Ion\nby the 1-(4-Methoxyphenyl)Ethyl Carbocation","volume":"125","author":"Tsuji","year":"2003","journal-title":"J. Am. Chem. Soc."},{"issue":"34","key":"2026090114375127800_cit43","doi-asserted-by":"publisher","first-page":"12972","DOI":"10.1021\/jp0478918","article-title":"Evidence of\nHeterogeneous Aggregation in Methanol\/CCl4 Mixtures: A\nBrillouin Scattering Investigation","volume":"108","author":"Aliotta","year":"2004","journal-title":"J. Phys.\nChem. B"},{"issue":"6","key":"2026090114375127800_cit44","doi-asserted-by":"publisher","first-page":"1318","DOI":"10.1021\/ja01539a010","article-title":"Infrared Measurements of the Association of Ethanol\nin Carbon Tetrachloride","volume":"80","author":"Coburn","year":"1958","journal-title":"J. Am. Chem. Soc."},{"issue":"2","key":"2026090114375127800_cit45","doi-asserted-by":"publisher","first-page":"96","DOI":"10.1002\/poc.610040205","article-title":"Taft\u2019s\nSubstituent Constants, \u03c3* and \u03c3I, and Huheey\u2019s\nGroup Electronegativity","volume":"4","author":"Datta","year":"1991","journal-title":"J. Phys. Org. Chem."},{"issue":"17","key":"2026090114375127800_cit46","doi-asserted-by":"publisher","first-page":"3039","DOI":"10.1021\/jp501636r","article-title":"Trends in Bond Dissociation Energies\nof Alcohols and Aldehydes Computed with Multireference Averaged Coupled-Pair\nFunctional Theory","volume":"118","author":"Oyeyemi","year":"2014","journal-title":"J. Phys. Chem. 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Chem."},{"issue":"6","key":"2026090114375127800_cit49","doi-asserted-by":"publisher","first-page":"577","DOI":"10.1002\/(SICI)1096-9888(199706)32:6&lt;577::AID-JMS530&gt;3.0.CO;2-4","article-title":"Ion Mobility Measurements and Their\nApplications to\nClusters and Biomolecules","volume":"32","author":"Clemmer","year":"1997","journal-title":"J. Mass Spectrom."},{"issue":"5","key":"2026090114375127800_cit50","doi-asserted-by":"publisher","first-page":"1633","DOI":"10.1039\/B914002F","article-title":"Ion\nMobility Mass Spectrometry of Proteins and Protein Assemblies","volume":"39","author":"Uetrecht","year":"2010","journal-title":"Chem. Soc. Rev."},{"issue":"23","key":"2026090114375127800_cit51","doi-asserted-by":"publisher","first-page":"4271","DOI":"10.1021\/jp970479q","article-title":"Unimolecular\nChemistry of Protonated\nDiols in the Gas Phase: Internal Cyclization and Hydride Ion Transfer","volume":"101","author":"Bouchoux","year":"1997","journal-title":"J. Phys. Chem. A"}],"container-title":["The Journal of Physical\nChemistry A"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jpca.6c02615","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article-pdf\/130\/34\/6807\/66739841\/acs.jpca.6c02615.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article-pdf\/130\/34\/6807\/66739841\/acs.jpca.6c02615.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T18:37:59Z","timestamp":1788287879000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article\/130\/34\/6807\/5268166\/Laser-Organic-Synthesis-of-Trichloromethyl"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,18]]},"references-count":51,"journal-issue":{"issue":"34","published-online":{"date-parts":[[2026,8,18]]},"published-print":{"date-parts":[[2026,8,27]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jpca.6c02615","relation":{},"ISSN":["1089-5639","1520-5215"],"issn-type":[{"value":"1089-5639","type":"print"},{"value":"1520-5215","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,18]]}}}