Recent Advances of Stable Phenoxyl Diradicals

doi:10.1007/s40242-023-3012-6

Abstract

Abstract: Organic radicals with unpaired electrons have shown great semiconducting properties with potential applications in the field of organic photodetectors, organic light-emitting diodes and organic spintronics. A major problem for limiting radicals from laboratory research to practical applications is the relatively low chemical and physical stabilities. Therefore, the right selection of radical core is the key to meaningful scientific research. Phenoxyl radical is one of the few stable radicals with spin distribution properties. Moreover, phenoxyl diradicals provide extract stability due to multiple resonance structures. Due to the long-distance spin distribution, which makes phenoxyl diradicals show interesting electronic and magnetic properties. In this review, we summarize the progress of phenoxyl diradicals in recent years in terms of syntheses, properties and future perspective.

Key words: Phenoxyl, Diradical, Conjugation, Stability

ZHANG Hanjun, MIAO Fang, LIU Xiaodong, WANG Dongsheng, ZHENG Yonghao. Recent Advances of Stable Phenoxyl Diradicals[J]. Chemical Research in Chinese Universities, 2023, 39(2): 170-175.

References

[1] Pummerer R., Frankfurter F., Ber. Dtsch. Chem. Ges., 1914, 47, 1472
[2] Altwicker E. R., Chem. Rev., 1967, 67, 475
[3] Reszka K. J., McGraw D. W., Britigan B. E., Chem. Res. Toxicol., 2009, 22, 1137
[4] Zurita D., Gautier I., Ménage S., Pierre J. L., Saint-Aman E., J. Biol. Inorg. Chem., 1997, 2, 46
[5] Shimazaki Y., Huth S., Hirota S., Yamauchi O., Inorg. Chim. Acta, 2002, 331, 168
[6] Kosower E. M., Poziomek E. J., J. Am. Chem. Soc., 1964, 86, 5515
[7] Abe M., Chem. Rev., 2013, 113, 7011
[8] Salem L., Rowland C., Angew. Chem. Int. Ed. Engl., 1972, 11, 92
[9] Suga T., Sugita S., Ohshiro H., Oyaizu K., Nishide H., Adv. Mater., 2011, 23, 751
[10] Anghel M., Magnan F., Catingan S. D., McCready M. A., Aawani E., Wong V., Singh D., Fanchini G., Gilroy J. B., J. Polym. Sci., 2020, 58, 309
[11] Liu R., Zhang C., Li L., Liao D., Sutter J. P., Dalton T., 2012, 41, 12139
[12] Shima Y., Suzuki T., Abe H., Yajima T., Mori S., Shimazaki Y., Chem. Commun., 2022, 58, 6401
[13] Remke S. C., Bürgin T. H., Ludvíková L., Heger D., Wenger O. S., von Gunten U., Canonica S., Water Res., 2022, 213, 118095
[14] Saito J., Mitani M., Mohri J. I., Yoshida Y., Matsui S., Ishii S. I., Kojoh S. I., Kashiwa N., Fujita T., Angew. Chem. Int. Ed. Engl., 2001, 40, 2918
[15] Musso H., Angew. Chem. Int. Ed. Engl., 1963, 2, 723
[16] Lavi A., Lin P., Bhaduri B., Carmieli R., Laskin A., Rudich Y., ACS Earth Space Chem., 2017, 1, 637
[17] Dol C., Bertrand M. P., Gastaldi S., Besson E., Tetrahedron, 2016, 72, 7744
[18] Cook C. D., Woodworth R. C., J. Am.Chem. Soc., 1953, 75, 6242
[19] Manda E., B. Chem. Soc. Jpn., 1974, 47, 2727
[20] Altwicker E. R., Chem. Rev., 1967, 67, 475
[21] Cook C. D., Nash N. G., Flanagan H. R., J. Am.Chem. Soc., 1955, 77, 1783
[22] Kobayashi Y., Shima K., Mutoh K., Abe J., J. Phys. Chem. Lett., 2016, 7, 3067
[23] Toshimitsu S., Shima K., Mutoh K., Kobayashi Y., Abe J., ChemPhotoChem, 2019, 3, 487
[24] Scott A. I., Quarterly Reviews, Chemical Society, 1965, 19, 1
[25] Ley K., Scheffler K., Rieker A., Müller E., Z. Naturforsch B, 1958, 13, 460
[26] Dimroth K., Berndt A., Bär F., Schweig A., Volland R., Angew. Chem. Int. Ed. Engl., 1967, 6, 34
[27] Müller E., Mayer R., Narr B., Rieker A., Scheffler K., Liebigs Ann. Chem., 1961, 645, 25
[28] Rieker A., Scheffler K., Tetrahedron Lett., 1965, 6, 1337
[29] Manner V. W., Markle T. F., Freudenthal J. H., Roth J. P., Mayer J. M., Chem. Commun(Camb), 2008, 256
[30] Hayashi T., Maeda K., Shida S., Nakada K., J. Chem. Phys., 1960, 32, 1568
[31] Fujita K., Hatano S., Kato D., Abe J., Org. Lett., 2008, 10, 3105
[32] Kawai T., Nakashima Y., Irie M., Adv. Mater., 2005, 17, 309
[33] Irie M., Fukaminato T., Sasaki T., Tamai N., Kawai T., Nature, 2002, 420, 759
[34] Nakahara I., Kikuchi A., Iwahori F., Abe J., Chem. Phys. Lett., 2005, 402, 107
[35] Yamashita H., Ikezawa T., Kobayashi Y., Abe J., J. Am.Chem. Soc., 2015, 137, 4952
[36] Blanco-Lomas M., Samanta S., Campos P. J., Woolley G. A., Sampedro D., J. Am.Chem. Soc., 2012, 134, 6960
[37] Deniz E., Tomasulo M., Cusido J., Sortino S., Raymo F. M., Langmuir, 2011, 27, 11773
[38] Mutoh K., Toshimitsu S., Kobayashi Y., Abe J., J. Am.Chem. Soc., 2021, 143, 13917
[39] Rausch R., Röhr M. I. S., Schmidt D., Krummenacher I., Braunschweig H., Würthner F., Chem. Sci., 2021, 12, 793
[40] Schmidt D., Son M., Lim J. M., Lin M.-J., Krummenacher I., Braunschweig H., Kim D., Würthner F., Angew. Chem. Int. Ed., 2015, 54, 13980
[41] Zhang K., Huang K.-W., Li J., Luo J., Chi C., Wu J., Org. Lett., 2009, 11, 4854
[42] Tampieri F., Colella L., Maghsoumi A., Martí-Rujas J., Parisini E., Tommasini M., Bertarelli C., Barbon A., J. Phys. Chem. C, 2016, 120, 5732
[43] Lee S., Miao F., Phan H., Herng T. S., Ding J., Wu J., Kim D., ChemPhysChem, 2017, 18, 591
[44] Miao F., Phan H., Wu J., Molecules, 2019, 24, 1446
[45] Xue G., Hu X., Chen H., Ge L., Wang W., Xiong J., Miao F., Zheng Y., Chem. Commun., 2020, 56, 5143
[46] Shen Y., Xue G., Dai Y., Quintero S. M., Chen H., Wang D., Miao F., Negri F., Zheng Y., Casado, J., Nat. Commun., 2021, 12, 6262
[47] Wang W., Ge L., Xue G., Miao F., Chen P., Chen H., Lin Y., Ni Y., Xiong J., Hu Y., Wu J., Zheng Y., Chem. Commun., 2020, 56, 1405
[48] Sakamaki D., Yano S., Kobashi T., Seki S., Kurahashi T., Matsubara S., Ito A., Tanaka K., Angew. Chem. Int. Ed., 2015, 127, 8385
[49] Ueda A., Nishida S., Fukui K., Ise T., Shiomi D., Sato K., Takui T., Nakasuji K., Morita Y., Angew. Chem. Int. Ed., 2010, 49, 1678
[50] Qiao Y., Guo Y., Yu C., Zhang F., Xu W., Liu Y., Zhu D., J. Am.Chem. Soc., 2012, 134, 4084
[51] Wang C., Zang Y., Qin Y., Zhang Q., Sun Y., Di C.-A., Xu W., Zhu D., Chem. Eur. J., 2014, 20, 13755
[52] Wang C., Qin Y., Sun Y., Guan Y.-S., Xu W., Zhu D., ACS Appl. Mater. Interfaces, 2015, 7, 15978
[53] Wu H., Wang Y., Qiao X., Wang D., Yang X., Li H., Chem. Mater., 2018, 30, 6992
[54] Wang K., Zhan Q., Han B., Quintero S. M., Huang W., Ji Y., Miao F., Chen H., Casado J., Zheng Y., J. Mater. Chem. C, 2022, 10, 12724
[55] Lin H. W., Ku S. Y., Su H. C., Huang C. W., Lin Y. T., Wong K. T., Wu C. C., Adv. Mater., 2005, 17, 2489
[56] Kubo T., Shimizu A., Sakamoto M., Uruichi M., Yakushi K., Nakano M., Shiomi D., Sato K., Takui T., Morita Y., Nakasuji K., Angew. Chem. Int. Ed., 2005, 117, 6722
[57] Koike H., Chikamatsu M., Azumi R., Tsutsumi J. Y., Ogawa K., Yamane W., Nishiuchi T., Kubo T., Hasegawa T., Kanai K., Adv. Funct. Mater., 2016, 26, 277
[58] Yamagishi M., Tominari Y., Uemura T., Yamada K., Takeya J., Jpn. J. Appl. Phys., 2010, 49, 01AB05
[59] Abe M., Ye J., Mishima M., Chem. Soc. Rev., 2012, 41, 3808
[60] Suga T., Ohshiro H., Sugita S., Oyaizu K., Nishide H., Adv. Mater., 2009, 21, 1627
[61] Imada Y., Nakano H., Furukawa K., Kishi R., Nakano M., Maruyama H., Nakamoto M., Sekiguchi A., Ogawa M., Ohta T., Yamamoto Y., J. Am.Chem. Soc., 2016, 138, 479
[62] Maruyama H., Nakano H., Nakamoto M., Sekiguchi A., Angew. Chem. Int. Ed., 2014, 53, 1324
[63] Bryan C. D., Cordes A. W., Fleming R. M., George N. A., Glarum S. H., Haddon R. C., Oakley R. T., Palstra T. T. M., Perel A. S., Schneemeyer L. F., Waszczak J. V., Nature, 1993, 365, 821
[64] Kobayashi Y., Terauchi T., Sumi S., Matsushita Y., Nat. Mater., 2017, 16, 109
[65] Low J. Z., Kladnik G., Patera L. L., Sokolov S., Lovat G., Kumarasamy E., Repp J., Campos L. M., Cvetko D., Morgante A., Venkataraman L., Nano Lett., 2019, 19, 2543
[66] Frisenda R., Gaudenzi R., Franco C., Mas-Torrent M., Rovira C., Veciana J., Alcon I., Bromley S. T., Burzurí E., van der Zant H. S. J., Nano Lett., 2015, 15, 3109
[67] Mannini M., Sorace L., Gorini L., Piras F. M., Caneschi A., Magnani A., Menichetti S., Gatteschi D., Langmuir, 2007, 23, 2389
[68] Liu J., Zhao X., Al-Galiby Q., Huang X., Zheng J., Li R., Huang C., Yang Y., Shi J., Manrique D. Z., Lambert C. J., Bryce M. R., Hong W., Angew. Chem. Int. Ed., 2017, 56, 13061