{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T13:07:50Z","timestamp":1785503270886,"version":"3.56.0"},"reference-count":50,"publisher":"American Chemical Society (ACS)","issue":"30","license":[{"start":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T00:00:00Z","timestamp":1784505600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100018992","name":"Fonds der Chemischen Industrie","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100018992","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["40\/575-1"],"award-info":[{"award-number":["40\/575-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["496207555"],"award-info":[{"award-number":["496207555"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Dr. Eberle Stiftung","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,7,31]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>1,2-Dihydro-1,2-azaborinines (BN-benzenes) are promising candidates for molecular solar thermal energy storage (MOST) as substitution-dependent isomerization to either the Dewar BN-benzene or benzvalene isomers is possible. Since not only photoisomerization behavior but also key MOST parameters, such as the half-life of the photoisomers, the energy storage density, and the absorption wavelength, are strongly influenced by substitution, a systematic investigation of structure\u2013property relationships is essential to accurately predict performance and design optimized storage systems. We report the synthesis of 1,2-disubstituted dihydroazaborinines varying steric demand at the 1- (nitrogen) and 2-position (boron) independently. Comprehensive investigations of their photoswitching behavior, half-life and stored energy of the metastable state demonstrated that a sterically demanding substituent at the boron atom is sufficient to stabilize the dihydroazaborinine itself under ambient conditions, while an additional bulky group at the nitrogen atom is required to suppress the spontaneous thermal back-reaction of the Dewar BN-benzene photoisomer at room temperature. Consequently, the steric demand of both substituents is crucial for achieving a promising MOST system.<\/jats:p>","DOI":"10.1021\/acs.joc.6c00925","type":"journal-article","created":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T13:35:41Z","timestamp":1784554541000},"page":"10454-10460","source":"Crossref","is-referenced-by-count":0,"title":["Substituent Tightrope:\nBalancing Energy Storage and\nStability of Dihydroazaborinine Molecular Solar Thermal Energy Storage\nCandidates"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5489-4570","authenticated-orcid":true,"given":"Sonja M.","family":"Biebl","sequence":"first","affiliation":[{"name":"Eberhard Karls Universita\u0308t Tu\u0308bingen , , Auf der Morgenstelle 18 , ,","place":["Tu\u0308bingen, Germany, 72076"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Niklas","family":"Thiess","sequence":"additional","affiliation":[{"name":"Eberhard Karls Universita\u0308t Tu\u0308bingen , , Auf der Morgenstelle 18 , ,","place":["Tu\u0308bingen, Germany, 72076"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kathrin","family":"Zwettler","sequence":"additional","affiliation":[{"name":"Eberhard Karls Universita\u0308t Tu\u0308bingen , , Auf der Morgenstelle 18 , ,","place":["Tu\u0308bingen, Germany, 72076"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5147-5677","authenticated-orcid":true,"given":"Markus","family":"Stro\u0308bele","sequence":"additional","affiliation":[{"name":"Eberhard Karls Universita\u0308t Tu\u0308bingen , , Auf der Morgenstelle 18 , ,","place":["Tu\u0308bingen, Germany, 72076"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5223-662X","authenticated-orcid":true,"given":"Holger F.","family":"Bettinger","sequence":"additional","affiliation":[{"name":"Eberhard Karls Universita\u0308t Tu\u0308bingen , , Auf der Morgenstelle 18 , ,","place":["Tu\u0308bingen, Germany, 72076"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,20]]},"reference":[{"issue":"9","key":"2026073108244009800_cit1","doi-asserted-by":"publisher","first-page":"3528","DOI":"10.1002\/chem.201405627","article-title":"BN Heterosuperbenzenes: Synthesis\nand Properties","volume":"21","author":"Wang","year":"2015","journal-title":"Chem.\u2500Eur. J."},{"issue":"4","key":"2026073108244009800_cit2","doi-asserted-by":"publisher","first-page":"1184","DOI":"10.1021\/jacs.7b09446","article-title":"The State of the\nArt in Azaborine Chemistry: New Synthetic\nMethods and Applications","volume":"140","author":"Giustra","year":"2018","journal-title":"J. Am. Chem. Soc."},{"issue":"1","key":"2026073108244009800_cit3","doi-asserted-by":"publisher","first-page":"8","DOI":"10.1139\/v08-110","article-title":"B-N as a C-C substitute\nin aromatic systems","volume":"87","author":"Bosdet","year":"2009","journal-title":"Can. J. Chem."},{"issue":"2","key":"2026073108244009800_cit4","doi-asserted-by":"publisher","first-page":"242","DOI":"10.1002\/anie.200703535","article-title":"B\u2013N versus\nC = C: How Similar Are They?","volume":"47","author":"Liu","year":"2008","journal-title":"Angew. Chem.,\nInt. Ed."},{"issue":"16","key":"2026073108244009800_cit5","doi-asserted-by":"publisher","first-page":"2927","DOI":"10.1002\/1521-3773(20020816)41:16&lt;2927::AID-ANIE2927&gt;3.0.CO;2-L","article-title":"Boron Chemistry\nLights the Way: Optical Properties\nof Molecular and Polymeric Systems","volume":"41","author":"Entwistle","year":"2002","journal-title":"Angew. Chem.,\nInt. Ed."},{"issue":"1","key":"2026073108244009800_cit6","doi-asserted-by":"publisher","first-page":"2","DOI":"10.1246\/cl.2005.2","article-title":"A Key Role of Orbital\nInteraction in the Main Group Element-containing\n\u03c0-Electron Systems","volume":"34","author":"Yamaguchi","year":"2005","journal-title":"Chem. Lett."},{"issue":"47","key":"2026073108244009800_cit7","doi-asserted-by":"publisher","first-page":"12955","DOI":"10.1021\/jp065085q","article-title":"\u03c3- and \u03c0-Bond\nStrengths in Main Group 3\u20135\nCompounds","volume":"110","author":"Grant","year":"2006","journal-title":"J. Phys. Chem. 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Catal."},{"issue":"36","key":"2026073108244009800_cit27","doi-asserted-by":"publisher","first-page":"24748","DOI":"10.1021\/jacs.4c08088","article-title":"A BN-Benzvalene","volume":"146","author":"Ozaki","year":"2024","journal-title":"J. Am. Chem.\nSoc."},{"issue":"46","key":"2026073108244009800_cit28","doi-asserted-by":"publisher","first-page":"8351","DOI":"10.1039\/D5CC01963J","article-title":"Rational design of\nred-shifted 1,2-azaborinine-based molecular solar thermals","volume":"61","author":"Mu\u0308ller","year":"2025","journal-title":"Chem. Commun."},{"issue":"3","key":"2026073108244009800_cit29","doi-asserted-by":"publisher","first-page":"825","DOI":"10.1039\/C1SC00500F","article-title":"BN-substituted diphenylacetylene: a basic model for\nconjugated \u03c0-systems containing the BN bond pair","volume":"3","author":"Marwitz","year":"2012","journal-title":"Chem. Sci."},{"issue":"34","key":"2026073108244009800_cit30","doi-asserted-by":"publisher","first-page":"12908","DOI":"10.1021\/ja4073436","article-title":"Protecting\nGroup-Free Synthesis of 1,2-Azaborines: A Simple Approach to the Construction\nof BN-Benzenoids","volume":"135","author":"Abbey","year":"2013","journal-title":"J. Am. Chem. Soc."},{"issue":"53","key":"2026073108244009800_cit31","doi-asserted-by":"publisher","first-page":"7258","DOI":"10.1039\/C6CC08599G","article-title":"High molecular\nweight poly(N-methyl-B-vinylazaborine)\n\u2013 a semi-inorganic B\u2013N polystyrene analogue","volume":"53","author":"Thiedemann","year":"2017","journal-title":"Chem. Commun."},{"issue":"35","key":"2026073108244009800_cit32","doi-asserted-by":"publisher","first-page":"14059","DOI":"10.1021\/jacs.1c06112","article-title":"The Versatile\nReaction Chemistry of an Alpha-Boryl Diazo Compound","volume":"143","author":"Liu","year":"2021","journal-title":"J. Am. Chem. Soc."},{"issue":"23","key":"2026073108244009800_cit33","doi-asserted-by":"publisher","first-page":"4905","DOI":"10.1021\/ol702383u","article-title":"Diversity\nthrough Isosterism: The Case of Boron-Substituted 1,2-Dihydro-1,2-azaborines","volume":"9","author":"Marwitz","year":"2007","journal-title":"Org. Lett."},{"issue":"42","key":"2026073108244009800_cit34","doi-asserted-by":"publisher","first-page":"15259","DOI":"10.1021\/jacs.7b09491","article-title":"A Boron Protecting Group Strategy for 1,2-Azaborines","volume":"139","author":"Baggett","year":"2017","journal-title":"J. Am. Chem. 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Bis(dialkylamino)-borfluoride","volume":"99","author":"No\u0308th","year":"1966","journal-title":"Chem. Ber."},{"issue":"7","key":"2026073108244009800_cit43","doi-asserted-by":"publisher","first-page":"1028","DOI":"10.1021\/ic50017a025","article-title":"Nuclear Magnetic Resonance Spectra\nof Phenylboronic\nAcids","volume":"3","author":"Beachell","year":"1964","journal-title":"Inorg. Chem."},{"issue":"20","key":"2026073108244009800_cit44","doi-asserted-by":"publisher","first-page":"3252","DOI":"10.1021\/jo00440a011","article-title":"Organoboranes.\n22.\nLight-induced reaction of bromine with alkylboronate esters. A convenient\nsynthesis of.alpha.-bromoalkylboronate esters","volume":"42","author":"Brown","year":"1977","journal-title":"J. Org. Chem."},{"issue":"3","key":"2026073108244009800_cit45","doi-asserted-by":"publisher","first-page":"235","DOI":"10.1016\/S0022-328X(00)88732-X","article-title":"Studies on trivalent boron compounds:\nI. The boron and proton magnetic resonance spectra of some trivalent\nboron compounds","volume":"6","author":"Moor","year":"1966","journal-title":"J. Organomet. Chem."},{"issue":"10","key":"2026073108244009800_cit46","doi-asserted-by":"publisher","first-page":"2408","DOI":"10.1021\/ja00986a029","article-title":"New heteroaromatic\ncompounds. XXV. Studies of salt formation in boron\noxyacids by boron-11 nuclear magnetic resonanceArticle link copied!","volume":"89","author":"Dewar","year":"1967","journal-title":"J. Am. Chem. Soc."},{"issue":"11","key":"2026073108244009800_cit47","doi-asserted-by":"publisher","first-page":"1303","DOI":"10.1039\/B904120F","article-title":"How stable are 1,2-dihydro-1,2-azaborines toward water\nand oxygen?","volume":"5","author":"Lamm","year":"2009","journal-title":"Mol. BioSyst."},{"key":"2026073108244009800_cit48","doi-asserted-by":"publisher","first-page":"646","DOI":"10.1021\/acs.orglett.5c04676","article-title":"Mallory-Type Reactivity of 1,2-Dihydroazaborinines:\n6\u03c0-Electrocyclization-[1,5]-H Shift Cascade toward BN-Doped\nPolycyclic Frameworks","volume":"28","author":"Biebl","year":"2026","journal-title":"Org. Lett."},{"issue":"3","key":"2026073108244009800_cit49","doi-asserted-by":"publisher","first-page":"673","DOI":"10.1021\/cr990416z","article-title":"Isokinetic Relationship, Isoequilibrium Relationship,\nand Enthalpy\u2013Entropy Compensation","volume":"101","author":"Liu","year":"2001","journal-title":"Chem.\nRev."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c00925","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/30\/10454\/66055861\/acs.joc.6c00925.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/30\/10454\/66055861\/acs.joc.6c00925.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T12:24:52Z","timestamp":1785500692000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/30\/10454\/5219964\/Substituent-Tightrope-Balancing-Energy-Storage-and"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,20]]},"references-count":50,"journal-issue":{"issue":"30","published-online":{"date-parts":[[2026,7,20]]},"published-print":{"date-parts":[[2026,7,31]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c00925","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,20]]}}}