{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,31]],"date-time":"2026-10-31T16:09:39Z","timestamp":1793462979743,"version":"4.5.0"},"reference-count":70,"publisher":"American Chemical Society (ACS)","issue":"36","license":[{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["BG16RFPR002-1.009-0003"],"award-info":[{"award-number":["BG16RFPR002-1.009-0003"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Heteroaryl 4-substituted azo phthalimides were designed as photoswitches to investigate how electronic asymmetry influences photoswitching behavior and thermal Z\/E relaxation. Systematic variation of the heteroaryl fragment from electron-rich pyrrole to electron-deficient imidazole and pyrazole and a symmetric bis-phthalimide system progressively modified \u03c0-delocalization across the azo chromophore. The compounds showed efficient E\/Z photoisomerization, reaching 78\u201388% Z-isomer populations, whereas the symmetric bis-phthalimide derivative showed limited photoswitching (34%) due to extensive overlap of the E and Z absorption bands. Arrhenius and Eyring analyses revealed pronounced differences in Z-isomer stability, with half-lives ranging from 0.20 to 356 h. Increasing electron-acceptor character generally enhanced thermal stability. However, the comparable activation barriers of the imidazole and symmetric bis-phthalimide derivatives, despite their different photochemical behavior, show that thermal relaxation cannot be rationalized solely by electronic asymmetry. DFT calculations further indicated that molecular geometry and electronic structure shape the thermal isomerization landscape. Relaxed potential-energy scans revealed a larger rotational contribution for the pyrrole derivative and mixed rotation\/inversion character for the remaining compounds. Thus, photoswitching is strongly governed by electronic asymmetry, whereas thermal stability reflects the combined effects of electronic structure, molecular geometry, and the ground-state potential-energy surface.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01333","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T10:18:16Z","timestamp":1788430696000},"page":"12235-12246","source":"Crossref","is-referenced-by-count":2,"title":["Electronic Asymmetry\nGoverns Photoswitching and Shapes\nThermal Relaxation in Heteroaryl Azo Phthalimides"],"prefix":"10.1021","volume":"91","author":[{"given":"Desislava","family":"Marinova","sequence":"first","affiliation":[{"name":"University of Chemical Technology and Metallurgy , , 8 St. Kliment Ohridski Blvd , ,","place":["Sofia, Bulgaria, 1756"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dragomir","family":"Borisov","sequence":"additional","affiliation":[{"name":"University of Chemical Technology and Metallurgy , , 8 St. Kliment Ohridski Blvd , ,","place":["Sofia, Bulgaria, 1756"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rebecca","family":"Strada","sequence":"additional","affiliation":[{"name":"University of Chemical Technology and Metallurgy , , 8 St. Kliment Ohridski Blvd , ,","place":["Sofia, Bulgaria, 1756"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9323-3521","authenticated-orcid":true,"given":"Kosuke","family":"Nakashima","sequence":"additional","affiliation":[{"name":"Tokyo University of Pharmacy and Life Sciences , , 1432-1 Horinouchi , , ,","place":["Hachioji, Tokyo, Japan, 192-0392"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miroslav","family":"Dangalov","sequence":"additional","affiliation":[{"name":"Bulgarian Academy of Sciences , , Acad. G. Bonchev Avenue, Bldg. 9 , ,","place":["Sofia, Bulgaria, 1113"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasuyuki","family":"Matsushima","sequence":"additional","affiliation":[{"name":"Tokyo University of Pharmacy and Life Sciences , , 1432-1 Horinouchi , , ,","place":["Hachioji, Tokyo, Japan, 192-0392"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8125-5010","authenticated-orcid":true,"given":"Shin-Ichi","family":"Hirashima","sequence":"additional","affiliation":[{"name":"Tokyo University of Pharmacy and Life Sciences , , 1432-1 Horinouchi , , ,","place":["Hachioji, Tokyo, Japan, 192-0392"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1216-4507","authenticated-orcid":true,"given":"Tsuyoshi","family":"Miura","sequence":"additional","affiliation":[{"name":"Tokyo University of Pharmacy and Life Sciences , , 1432-1 Horinouchi , , ,","place":["Hachioji, Tokyo, Japan, 192-0392"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7197-8389","authenticated-orcid":true,"given":"Anton","family":"Georgiev","sequence":"additional","affiliation":[{"name":"University of Chemical Technology and Metallurgy , , 8 St. Kliment Ohridski Blvd , ,","place":["Sofia, Bulgaria, 1756"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,1]]},"reference":[{"key":"2026091109105205000_cit1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527827626","volume-title":"Molecular\nPhotoswitches: chemistry, Properties, and Applications, 2 Volume Set","author":"Pianowski","year":"2022"},{"issue":"3537","key":"2026091109105205000_cit2","doi-asserted-by":"publisher","first-page":"281","DOI":"10.1038\/140281a0","article-title":"The Cis-Form\nof Azobenzene","volume":"140","author":"Hartley","year":"1937","journal-title":"Nature"},{"issue":"31","key":"2026091109105205000_cit3","doi-asserted-by":"publisher","first-page":"8094","DOI":"10.1002\/CHEM.202005486","article-title":"Fluorinated\nAzobenzenes Switchable with Red Light","volume":"27","author":"Leistner","year":"2021","journal-title":"Chem.\u2013Eur.\nJ."},{"issue":"29","key":"2026091109105205000_cit4","doi-asserted-by":"publisher","first-page":"19609","DOI":"10.1021\/jacs.4c03135","article-title":"Visible-Light-Activated\nHeteroaryl\nAzoswitches: Toward a More Colorful Future","volume":"146","author":"Dang","year":"2024","journal-title":"J. Am. Chem. Soc."},{"issue":"48","key":"2026091109105205000_cit5","doi-asserted-by":"publisher","first-page":"21663","DOI":"10.1002\/anie.202008700","article-title":"General Principles for the Design\nof Visible-Light-Responsive Photoswitches: Tetra-Ortho-Chloro-Azobenzenes","volume":"59","author":"Lameijer","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"issue":"39","key":"2026091109105205000_cit6","doi-asserted-by":"publisher","first-page":"11338","DOI":"10.1002\/anie.201500628","article-title":"Visible-Light-Activated\nMolecular Switches","volume":"54","author":"Ble\u0301ger","year":"2015","journal-title":"Angew. Chem., Int. Ed."},{"issue":"51","key":"2026091109105205000_cit7","doi-asserted-by":"publisher","first-page":"20597","DOI":"10.1021\/ja310323y","article-title":"O -Fluoroazobenzenes\nas Readily Synthesized Photoswitches Offering Nearly Quantitative\nTwo-Way Isomerization with Visible Light","volume":"134","author":"Ble\u0301ger","year":"2012","journal-title":"J.\nAm. Chem. Soc."},{"issue":"33","key":"2026091109105205000_cit8","doi-asserted-by":"publisher","first-page":"7039","DOI":"10.1364\/AO.44.007039","article-title":"Optically\nReconfigurable Azobenzene Polymer-Based Fiber Bragg Filter","volume":"44","author":"Lausten","year":"2005","journal-title":"Appl. Opt."},{"issue":"2","key":"2026091109105205000_cit9","doi-asserted-by":"publisher","first-page":"227","DOI":"10.1007\/s00340-015-6046-8","article-title":"Photoinduced Birefringence\nof Azobenzene Polymer at Blue Excitation Wavelengths","volume":"119","author":"Kozanecka-Szmigiel","year":"2015","journal-title":"Appl. Phys. B"},{"issue":"5219","key":"2026091109105205000_cit10","doi-asserted-by":"publisher","first-page":"1873","DOI":"10.1126\/science.268.5219.1873","article-title":"Optical Switching and\nImage Storage by Means of Azobenzene\nLiquid-Crystal Films","volume":"268","author":"Ikeda","year":"1995","journal-title":"Science"},{"issue":"39","key":"2026091109105205000_cit11","doi-asserted-by":"publisher","first-page":"52945","DOI":"10.1021\/acsami.4c11876","article-title":"Photoinduced\nBirefringence and Liquid Crystal Orientation on Polymers with Different\nAzobenzene Content in the Main Chain","volume":"16","author":"Tkachenko","year":"2024","journal-title":"ACS Appl.\nMater. Interfaces"},{"issue":"42","key":"2026091109105205000_cit12","doi-asserted-by":"publisher","first-page":"38677","DOI":"10.1021\/jacs.5c12874","article-title":"Reversible\nSingle-Crystal-to-Single-Crystal Isomerization of the Azo Photoswitch","volume":"147","author":"Dang","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"11","key":"2026091109105205000_cit13","doi-asserted-by":"publisher","DOI":"10.1002\/ADOM.202503223","article-title":"Visible-Light-Driven\nHeteroaryl Azo Switches with High-Efficiency Photoisomerization for\nAdvanced Photochromic Systems","volume":"14","author":"Lv","year":"2026","journal-title":"Adv. Opt. Mater."},{"issue":"16","key":"2026091109105205000_cit14","doi-asserted-by":"publisher","first-page":"1900404","DOI":"10.1002\/adom.201900404","article-title":"Designing Molecular\nPhotoswitches for Soft Materials Applications","volume":"7","author":"Boelke","year":"2019","journal-title":"Adv. Opt. Mater."},{"issue":"31","key":"2026091109105205000_cit15","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202404528","article-title":"Solar Azo-Switches\nfor Effective E\u2192Z Photoisomerization by Sunlight","volume":"63","author":"Zhang","year":"2024","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026091109105205000_cit16","doi-asserted-by":"publisher","first-page":"173","DOI":"10.1016\/j.eurpolymj.2019.03.028","article-title":"Azobenzene\nvs Azopyridine and Matrix Molar Masses Effect on Photoinduced Phenomena","volume":"115","author":"Bujak","year":"2019","journal-title":"Eur. Polym. J."},{"issue":"25","key":"2026091109105205000_cit17","doi-asserted-by":"publisher","first-page":"6494","DOI":"10.1002\/chem.201704162","article-title":"Photoinduced\nLiquefaction of Azobenzene-Containing\nPolymers","volume":"24","author":"Weis","year":"2018","journal-title":"Chem.\u2013Eur. J."},{"issue":"4","key":"2026091109105205000_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/smo.20240058","article-title":"Visible Light-Responsive\nAzo-Based Smart Materials: Design, Performance, and Applications in\nEnergy Storage","volume":"2","author":"Lv","year":"2024","journal-title":"Smart Mol."},{"issue":"1","key":"2026091109105205000_cit19","doi-asserted-by":"publisher","first-page":"100","DOI":"10.1016\/j.neuron.2016.08.038","article-title":"How Azobenzene Photoswitches\nRestore Visual Responses\nto the Blind Retina","volume":"92","author":"Tochitsky","year":"2016","journal-title":"Neuron"},{"issue":"24","key":"2026091109105205000_cit20","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202423506","article-title":"Manipulation\nof Chemistry and Biology with Visible Light Using Tetra-Ortho-Substituted\nAzobenzenes and Azonium Ions","volume":"64","author":"Cardano","year":"2025","journal-title":"Angew. Chem.,\nInt. Ed."},{"key":"2026091109105205000_cit21","doi-asserted-by":"publisher","first-page":"549","DOI":"10.1007\/s00726-018-02691-1","article-title":"Characterization\nand Anticonvulsant Activity of New Azobenzene-Containing VV-Hemorphin-5\nBio Photoswitch","volume":"51","author":"Todorov","year":"2019","journal-title":"Amino Acids"},{"issue":"36","key":"2026091109105205000_cit22","doi-asserted-by":"publisher","first-page":"32689","DOI":"10.1021\/jacs.5c08259","article-title":"A Versatile One-Pot Strategy for\nThiazolylazo Extensions:\nVisible Light-Driven Photoswitches","volume":"147","author":"Sahu","year":"2025","journal-title":"J. Am. Chem.\nSoc."},{"issue":"9","key":"2026091109105205000_cit23","doi-asserted-by":"publisher","first-page":"1814","DOI":"10.1021\/acs.jpca.8b11734","article-title":"Unraveling\nthe Thermal Isomerization Mechanisms of Heteroaryl Azoswitches: Phenylazoindoles\nas Case Study","volume":"123","author":"Crespi","year":"2019","journal-title":"J. Phys. Chem. A"},{"issue":"8","key":"2026091109105205000_cit24","doi-asserted-by":"publisher","first-page":"2940","DOI":"10.1021\/jacs.7b12871","article-title":"Tuning the\nThermal Isomerization of Phenylazoindole Photoswitches from Days to\nNanoseconds","volume":"140","author":"Simeth","year":"2018","journal-title":"J. Am. Chem. Soc."},{"issue":"3","key":"2026091109105205000_cit25","doi-asserted-by":"publisher","first-page":"1261","DOI":"10.1021\/jacs.6b11626","article-title":"Tuning Azoheteroarene Photoswitch Performance through\nHeteroaryl Design","volume":"139","author":"Calbo","year":"2017","journal-title":"J. Am. Chem. Soc."},{"issue":"10","key":"2026091109105205000_cit26","doi-asserted-by":"publisher","first-page":"6541","DOI":"10.1021\/acs.joc.2c00088","article-title":"Structure\u2013Property\nRelationship for Visible Light Bidirectional Photoswitchable Azoheteroarenes\nand Thermal Stability of Z-Isomers","volume":"87","author":"Gaur","year":"2022","journal-title":"J. Org.\nChem."},{"issue":"19","key":"2026091109105205000_cit27","doi-asserted-by":"publisher","first-page":"7635","DOI":"10.1021\/acs.orglett.1c02856","article-title":"Photoswitching of Ortho-Aminated\nArylazopyrazoles with Red Light","volume":"23","author":"Simke","year":"2021","journal-title":"Org. Lett."},{"issue":"8","key":"2026091109105205000_cit28","doi-asserted-by":"publisher","first-page":"1403","DOI":"10.1021\/jp066816p","article-title":"Photoisomerization\nand Thermal Isomerization of Arylazoimidazoles","volume":"111","author":"Otsuki","year":"2007","journal-title":"J. Phys. Chem. A"},{"issue":"19","key":"2026091109105205000_cit29","doi-asserted-by":"publisher","first-page":"10584","DOI":"10.1021\/jacs.2c13733","article-title":"Bistable Aryl Azopyrazolium Ionic\nPhotoswitches in Water","volume":"145","author":"Gaur","year":"2023","journal-title":"J. Am. Chem. Soc."},{"issue":"34","key":"2026091109105205000_cit30","doi-asserted-by":"publisher","first-page":"11878","DOI":"10.1021\/ja505444d","article-title":"Arylazopyrazoles:\nAzoheteroarene Photoswitches Offering Quantitative Isomerization and\nLong Thermal Half-Lives","volume":"136","author":"Weston","year":"2014","journal-title":"J. Am. Chem. Soc."},{"issue":"42","key":"2026091109105205000_cit31","doi-asserted-by":"publisher","first-page":"29237","DOI":"10.1021\/jacs.4c12532","article-title":"Photoswitchable\nAzobispyrazole Crystals Achieving Near-Quantitative Crystalline-State\nBidirectional E \u21c6 Z Conversions","volume":"146","author":"He","year":"2024","journal-title":"J. Am.\nChem. Soc."},{"issue":"45","key":"2026091109105205000_cit32","doi-asserted-by":"publisher","first-page":"42024","DOI":"10.1021\/jacs.5c15522","article-title":"Modular One-Pot Construction of Solar Azo-Switches Based on Heteroaryl\nOrganozinc Reagents","volume":"147","author":"Zhang","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"30","key":"2026091109105205000_cit33","doi-asserted-by":"publisher","first-page":"16675","DOI":"10.1002\/ange.202103705","article-title":"Azobispyrazole\nFamily as Photoswitches Combining (Near-) Quantitative\nBidirectional Isomerization and Widely Tunable Thermal Half-Lives\nfrom Hours to Years**","volume":"133","author":"He","year":"2021","journal-title":"Angew. Chem."},{"issue":"42","key":"2026091109105205000_cit34","doi-asserted-by":"publisher","first-page":"19777","DOI":"10.1039\/D5SC05070G","article-title":"Aryl Azopyrroles\nas Visible Light Photoswitchable TRPA1 Ligands","volume":"16","author":"Dollhopf","year":"2025","journal-title":"Chem. Sci."},{"issue":"39","key":"2026091109105205000_cit35","doi-asserted-by":"publisher","first-page":"35493","DOI":"10.1021\/jacs.5c09852","article-title":"Triplet\nSpin Delocalization and Temperature Dependence for Adiabatic and Non-Adiabatic\nZ\u2013E Isomerization Pathways in Azoarenes","volume":"147","author":"Martins","year":"2025","journal-title":"J. Am. Chem. Soc."},{"issue":"46","key":"2026091109105205000_cit36","doi-asserted-by":"publisher","first-page":"10882","DOI":"10.1021\/acs.jpclett.2c02838","article-title":"Solving the Azobenzene\nEntropy Puzzle: Direct Evidence for Multi-State Reactivity","volume":"13","author":"Reimann","year":"2022","journal-title":"J. Phys. Chem. Lett."},{"issue":"31","key":"2026091109105205000_cit37","doi-asserted-by":"publisher","first-page":"314002","DOI":"10.1088\/1361-648X\/aa75bd","article-title":"Thermal Isomerization\nof Azobenzenes: On the Performance of Eyring Transition State Theory","volume":"29","author":"Rietze","year":"2017","journal-title":"J. Phys.: Condens. Matter"},{"issue":"43","key":"2026091109105205000_cit38","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202514433","article-title":"Mechanistic\nInsight into Para-Substituent Control of Thermal Half-Lives in Arylazopyrazole\nPhotoswitches","volume":"64","author":"Schlo\u0308gl","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"issue":"41","key":"2026091109105205000_cit39","doi-asserted-by":"publisher","first-page":"19448","DOI":"10.1039\/D5SC04412J","article-title":"Azobisheteroarene\nPhotoswitches Based on Isoxazoles and Pyrazoles: Tunable Photostationary\nStates, Thermal Relaxation and Sensitization under Confinement","volume":"16","author":"Seyfried","year":"2025","journal-title":"Chem. Sci."},{"issue":"10","key":"2026091109105205000_cit40","doi-asserted-by":"publisher","first-page":"3234","DOI":"10.1021\/ja038327y","article-title":"On the Mechanism of the Cis\u2013trans\nIsomerization\nin the Lowest Electronic States of Azobenzene: S0, S1, and T1","volume":"126","author":"Cembran","year":"2004","journal-title":"J. Am. Chem. Soc."},{"issue":"22","key":"2026091109105205000_cit41","doi-asserted-by":"publisher","first-page":"4555","DOI":"10.1021\/jp027707n","article-title":"Mechanism of Cis-to-Trans\nIsomerization of Azobenzene: Direct MD Study","volume":"107","author":"Ikegami","year":"2003","journal-title":"J. Phys. Chem. A"},{"issue":"24","key":"2026091109105205000_cit42","doi-asserted-by":"publisher","first-page":"6763","DOI":"10.1021\/jp9021344","article-title":"Quantum Chemical\nInvestigation of\nThermal Cis-to-Trans Isomerization of Azobenzene Derivatives: Substituent\nEffects, Solvent Effects, and Comparison to Experimental Data","volume":"113","author":"Dokic\u0301","year":"2009","journal-title":"J. Phys. Chem. A"},{"issue":"21","key":"2026091109105205000_cit43","doi-asserted-by":"publisher","first-page":"7081","DOI":"10.1021\/ACS.JOC.5C00731","article-title":"Computational Rational Design of\nBridgehead Nitrogen Heterocyclic Azobenzene Photoswitches","volume":"90","author":"Pupavac","year":"2025","journal-title":"J. Org. Chem."},{"issue":"21","key":"2026091109105205000_cit44","doi-asserted-by":"publisher","first-page":"11580","DOI":"10.1039\/C8RA01132J","article-title":"Theoretical\nStudy on the Reaction Mechanism of the Thermal Cis\u2013Trans Isomerization\nof Fluorine-Substituted Azobenzene Derivatives","volume":"8","author":"Liu","year":"2018","journal-title":"RSC Adv."},{"issue":"5","key":"2026091109105205000_cit45","doi-asserted-by":"publisher","first-page":"1809","DOI":"10.1039\/C1CS15179G","article-title":"Photoisomerization in Different Classes of Azobenzene","volume":"41","author":"Bandara","year":"2012","journal-title":"Chem. Soc. Rev."},{"issue":"1","key":"2026091109105205000_cit46","doi-asserted-by":"publisher","first-page":"207","DOI":"10.1039\/D4OB01573H","article-title":"Azophotoswitches\nContaining Thiazole, Isothiazole, Thiadiazole, and Isothiadiazole","volume":"23","author":"Cheruthu","year":"2024","journal-title":"Org. Biomol. Chem."},{"issue":"16","key":"2026091109105205000_cit47","doi-asserted-by":"publisher","first-page":"9072","DOI":"10.1021\/jacs.3c00609","article-title":"Phenylazothiazoles\nas Visible-Light Photoswitches","volume":"145","author":"Lin","year":"2023","journal-title":"J. Am. Chem.\nSoc."},{"issue":"3","key":"2026091109105205000_cit48","doi-asserted-by":"publisher","first-page":"133","DOI":"10.1038\/s41570-019-0074-6","article-title":"Heteroaryl Azo Dyes as Molecular\nPhotoswitches","volume":"3","author":"Crespi","year":"2019","journal-title":"Nat. Rev. Chem."},{"issue":"35","key":"2026091109105205000_cit49","doi-asserted-by":"publisher","first-page":"8064","DOI":"10.1021\/jp0531917","article-title":"Photochromism of 2-(Phenylazo)Imidazoles","volume":"109","author":"Otsuki","year":"2005","journal-title":"J.\nPhys. Chem. A"},{"issue":"13","key":"2026091109105205000_cit50","doi-asserted-by":"publisher","first-page":"8236","DOI":"10.1021\/acs.joc.3c00211","article-title":"Photoisomerization of 2-Arylazoimidazoles under Visible\nLight: Identifying a Predictive Tool to Anticipate and Tune Likely\nPhotoswitching Performance and Cis Half-Life","volume":"88","author":"Dolai","year":"2023","journal-title":"J. Org. Chem."},{"key":"2026091109105205000_cit51","doi-asserted-by":"publisher","first-page":"1426","DOI":"10.1039\/D5RE00434A","article-title":"Visible-Light Azoarene Photoswitch Engineering by Heteroaryl\nDesign","volume":"11","author":"Hashim","year":"2026","journal-title":"React. Chem. Eng."},{"issue":"34","key":"2026091109105205000_cit52","doi-asserted-by":"publisher","first-page":"15620","DOI":"10.1039\/D5SC03275J","article-title":"Visible-Light-Responsive Indoleazopyrazole Photoswitches: Dual Enhancement\nof Redshift and Half-Life by Ester Modification at the Ortho Position","volume":"16","author":"Yu","year":"2025","journal-title":"Chem. Sci."},{"key":"2026091109105205000_cit53","doi-asserted-by":"publisher","first-page":"115390","DOI":"10.1016\/j.jphotochem.2023.115390","article-title":"Molecular\nAzo\u2013Imidazole Photoswitches: Property Tuning by Substitution","volume":"449","author":"Jeli\u0301nkova\u0301","year":"2024","journal-title":"J. Photochem. Photobiol., A"},{"issue":"1","key":"2026091109105205000_cit54","doi-asserted-by":"publisher","first-page":"7","DOI":"10.3762\/bxiv.2025.7.v1","article-title":"Substituent\nEffects in Acetylated Phenyl Azopyrazole Photoswitches","volume":"2025","author":"Tovtik","year":"2025","journal-title":"Beilstein Archives"},{"issue":"24","key":"2026091109105205000_cit55","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202301992","article-title":"Thiazolylazopyrazoles as Nonsymmetric\nBis-Heteroaryl Azo Switches:\nHigh-Yield Visible-Light Photoisomerization and Increased Z-Isomer\nStability by o-Carbonylation","volume":"62","author":"Dang","year":"2023","journal-title":"Angew. Chem.,\nInt. Ed."},{"issue":"40","key":"2026091109105205000_cit56","doi-asserted-by":"publisher","first-page":"8956","DOI":"10.1021\/acs.jpclett.3c01785","article-title":"Singlet and Triplet Pathways Determine the Thermal\nZ\/E Isomerization of an Arylazopyrazole-Based Photoswitch","volume":"14","author":"Singer","year":"2023","journal-title":"J. Phys. Chem. Lett."},{"issue":"37","key":"2026091109105205000_cit57","doi-asserted-by":"publisher","first-page":"12904","DOI":"10.1021\/acs.joc.5c01018","article-title":"Visible Light\nSwitching of Ortho-Functionalized Azo Phthalimides with Tunable Z-Isomer\nStability","volume":"90","author":"Yordanov","year":"2025","journal-title":"J. Org. Chem."},{"issue":"29","key":"2026091109105205000_cit58","doi-asserted-by":"publisher","DOI":"10.1002\/CHEM.202500435","article-title":"Synthesis and Properties\nof Cyclic Imide Extended Diazocines: Tweezer-Like, Rigid Photoswitches\nwith Large Switching Amplitudes","volume":"31","author":"Businski","year":"2025","journal-title":"Chem.\u2013Eur.\nJ."},{"issue":"32","key":"2026091109105205000_cit59","doi-asserted-by":"publisher","first-page":"22809","DOI":"10.1039\/D4RA03859B","article-title":"Phthalimides:\nDevelopments in Synthesis and Functionalization","volume":"14","author":"Doraghi","year":"2024","journal-title":"RSC Adv."},{"issue":"44","key":"2026091109105205000_cit60","doi-asserted-by":"publisher","first-page":"20519","DOI":"10.1039\/D1NJ03924E","article-title":"Beyond Conventional\nConstruction of the Phthalimide Core: A Review","volume":"45","author":"Das","year":"2021","journal-title":"New J. Chem."},{"issue":"21","key":"2026091109105205000_cit61","doi-asserted-by":"publisher","first-page":"7206","DOI":"10.1021\/ja810050y","article-title":"Phthalimide-Based\nPolymers for High Performance Organic Thin-Film Transistors","volume":"131","author":"Guo","year":"2009","journal-title":"J. Am. Chem. Soc."},{"issue":"24","key":"2026091109105205000_cit62","doi-asserted-by":"publisher","first-page":"17206","DOI":"10.1021\/acs.joc.3c02056","article-title":"Fluorescent Rotary\nSwitches: Four- vs Three-Substituted Phthalimide Boron Difluoride\nSchiff Base Complexes","volume":"88","author":"Yordanov","year":"2023","journal-title":"J. Org. Chem."},{"issue":"10","key":"2026091109105205000_cit63","doi-asserted-by":"publisher","first-page":"2499","DOI":"10.1021\/ja01106a503","article-title":"4-Nitrophthalimides. I. Derivatives of Alkyl Halides\nGiving a Saponification Equivalent","volume":"75","author":"Billman","year":"1953","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026091109105205000_cit64","doi-asserted-by":"publisher","first-page":"79","DOI":"10.1039\/JR9310000079","article-title":"XI.\u2500The Preparation of 4-Nitrophthalimide and\nDerivatives","author":"Levy","year":"1931","journal-title":"J. Chem. Soc"},{"key":"2026091109105205000_cit65","doi-asserted-by":"publisher","first-page":"240","DOI":"10.1016\/j.dyepig.2017.07.013","article-title":"Synthesis of Phthalimide Disperse\nDyes and Study on the Interaction Energy","volume":"146","author":"Zhan","year":"2017","journal-title":"Dyes\nPigm."},{"issue":"50","key":"2026091109105205000_cit66","doi-asserted-by":"publisher","first-page":"16492","DOI":"10.1002\/CHEM.201404649","article-title":"Ortho-Fluoroazobenzenes:\nVisible Light Switches with Very Long-Lived Z Isomers","volume":"20","author":"Knie","year":"2014","journal-title":"Chem.\u2013Eur. J."},{"issue":"10","key":"2026091109105205000_cit67","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202301714","article-title":"In-Situ Oxidation\nand Coupling of Anilines towards Unsymmetric Azobenzenes Using Flow\nChemistry","volume":"17","author":"Griwatz","year":"2024","journal-title":"ChemSusChem"},{"issue":"35","key":"2026091109105205000_cit68","doi-asserted-by":"publisher","first-page":"7575","DOI":"10.1039\/D1OB01450A","article-title":"Calculated Oxidation Potentials Predict\nReactivity\nin Baeyer\u2013Mills Reactions","volume":"19","author":"Tombari","year":"2021","journal-title":"Org. Biomol.\nChem"},{"key":"2026091109105205000_cit69","volume-title":"Modern Physical Organic\nChemistry","author":"Anslyn","year":"2005","edition":"1st"},{"issue":"14","key":"2026091109105205000_cit70","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202523613","article-title":"The Nonadiabatic Nature of the Substituent Effects\nin Azobenzene","volume":"65","author":"van der Wal","year":"2026","journal-title":"Angew. Chem., Int. Ed."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c01333","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/36\/12235\/68101366\/acs.joc.6c01333.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/36\/12235\/68101366\/acs.joc.6c01333.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T13:35:23Z","timestamp":1789133723000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/36\/12235\/5395756\/Electronic-Asymmetry-Governs-Photoswitching-and"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,1]]},"references-count":70,"journal-issue":{"issue":"36","published-online":{"date-parts":[[2026,9,1]]},"published-print":{"date-parts":[[2026,9,11]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c01333","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,1]]}}}