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The initial solid state of <jats:bold>1\u2010C<jats:sub>5<\/jats:sub>\u22c5<jats:sup>+<\/jats:sup><\/jats:bold>\u2009\u22c5\u2009NTf<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup> exhibited strong absorption in the near\u2010infrared (NIR; 700\u20131000\u2005nm) and SWIR regions, whereas the absorption in the SWIR region was significantly diminished in the stimulated state induced by dichloromethane vapor. Upon cessation of vapor stimulation, the solid state spontaneously and promptly reverted to its original state, characterized by absorption bands in the NIR\/SWIR region. Moreover, the SWIR absorption was absent upon the application of mechanical stress using a steel spatula. The reversal was fast and occurred within 10\u2005s. These changes were visualized using a SWIR imaging camera under 1450\u2010nm light irradiation. Experimental investigations demonstrated that the transparency to the SWIR light in the solid states was modulated through significant structural transformations of the associated radical cations, with transitions between columnar and isolated \u03c0\u2010dimer structures under ambient and stimulated conditions, respectively.<\/jats:p>","DOI":"10.1002\/anie.202308570","type":"journal-article","created":{"date-parts":[[2023,7,12]],"date-time":"2023-07-12T12:55:16Z","timestamp":1689166516000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["On\u2010Demand Control of Short\u2010Wave Infrared Light Transparency Based on Stimuli\u2010Responsive Association of Tetrathiafulvalene Radical Cations"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6294-9084","authenticated-orcid":false,"given":"Shuichi","family":"Suzuki","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Engineering Science Osaka University  Toyonaka Osaka 560\u20138531 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toshihiro","family":"Sakai","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Engineering Science Osaka University  Toyonaka Osaka 560\u20138531 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sota","family":"Takagi","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Engineering Science Osaka University  Toyonaka Osaka 560\u20138531 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5348-3390","authenticated-orcid":false,"given":"Takeshi","family":"Naota","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Engineering Science Osaka University  Toyonaka Osaka 560\u20138531 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,7,21]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00014a003"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200900596"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35211g"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00017a020"},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","unstructured":"Z.\u2005Y. Wang Near-Infrared Organic Materials and Emerging Applications CRC Press Boca Raton 2013.","DOI":"10.1201\/b14775"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/op800077j"},{"key":"e_1_2_7_8_1","unstructured":"\u00a0"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0731470"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/nl9024853"},{"key":"e_1_2_7_11_1","first-page":"739","volume":"105","author":"Peng Z.","year":"1996","journal-title":"Bull. Soc. Chim. Belg."},{"key":"e_1_2_7_12_1","unstructured":"\u00a0"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/0143-7208(94)00068-D"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat2272"},{"key":"e_1_2_7_15_1","unstructured":"Near-Infrared Spectroscopy(Eds.: Y. Ozaki C.Huck S. Tsuchikawa) Springer Singapore 2021."},{"key":"e_1_2_7_16_1","unstructured":"\u00a0"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c5pp00132c"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1RA00579K"},{"key":"e_1_2_7_19_1","unstructured":"\u00a0"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00394B"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3nr02286b"},{"key":"e_1_2_7_22_1","unstructured":"\u00a0"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1059552"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm801911n"},{"key":"e_1_2_7_25_1","unstructured":"\u00a0"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev-matsci-062910-100344"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.20180187"},{"key":"e_1_2_7_28_1","unstructured":"\u00a0"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar9600446"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0364928"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b00816"},{"key":"e_1_2_7_32_1","unstructured":"\u00a0"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502180"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmat2067"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41535-017-0033-8"},{"key":"e_1_2_7_36_1","unstructured":"\u00a0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201107265"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7RA12600J"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201900513"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201905465"},{"key":"e_1_2_7_41_1","unstructured":"\u00a0"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603409"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710354"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7TC01270E"},{"key":"e_1_2_7_45_1","unstructured":"\u00a0"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.9b00982"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202016930"},{"key":"e_1_2_7_48_1","unstructured":"TTF Chemistry(Eds.: J. Yamada T. Sugimoto ) Kodansha Tokyo 2004."},{"key":"e_1_2_7_49_1","unstructured":"For instance of optical waveguide spectroscopy see following references;"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2007.116"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1996.105"},{"key":"e_1_2_7_52_1","unstructured":"The neat film of1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212for exposure to dichloromethane vapor was prepared from the liquid state. The liquid state of radical cation salt1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212(mp. 68\u201370\u2009\u00b0C) was generated at 80\u2009\u00b0C and spread using a steel spatula over the glass plate. The plate was cooled to room temperature to afford the initial brown solid. Notably radical cation salt1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212did not decompose upon heating to 80\u2009\u00b0C: no weight loss was observed up to 150\u2009\u00b0C in the thermogravimetry measurement (Figure\u2005S20)."},{"key":"e_1_2_7_53_1","unstructured":"The green solid of1-C3\u22c5+\u2009\u22c5\u2009NTf2\u2212-Gdid not change to the brown solid which exhibited SWIR absorption upon exposure to cyclohexane vapor. This indicated that the pre-associated structure was important for modifying the SWIR absorption by external stimuli."},{"key":"e_1_2_7_54_1","unstructured":"Deposition numbers2266175 (1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212) 2266176 (1-C1\u22c5+\u2009\u22c5\u2009NTf2\u2212) 2266177 (1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212-B) and 2266178 (1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212-G)contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."},{"key":"e_1_2_7_55_1","unstructured":"The ESR signal of1-C3\u22c5+\u2009\u22c5\u2009NTf2\u2212-Bin the initial solid state was broad similar to that in the case of1-C5\u22c5+\u2009\u22c5\u2009NTf2\u2212."},{"key":"e_1_2_7_56_1","unstructured":"We also prepared SbF6\u2212and BF4\u2212salts of1-C5\u22c5+. The NIR\/SWIR absorption of the SbF6\u2212salt changed upon the application of mechanostress (Figure\u2005S21). However the stimulated state did not return to the original state. The BF4\u2212salt did not exhibit any change in the NIR\/SWIR absorption by the applications of external stimuli (Figure\u2005S22)."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202308570","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,11,15]],"date-time":"2023-11-15T20:34:57Z","timestamp":1700080497000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202308570"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,7,21]]},"references-count":56,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2023,8,28]]}},"alternative-id":["10.1002\/anie.202308570"],"URL":"https:\/\/doi.org\/10.1002\/anie.202308570","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,7,21]]},"assertion":[{"value":"2023-06-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-07-21","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202308570"}}