Ultrasound-induced circularly polarized luminescence based on homochiral aggregation of clothespin-shaped Pt(II) complexes

Abstract

Ultrasound-induced circularly polarized luminescence (CPL) was achieved using planar chiral, binuclear clothespin-shaped trans-bis(salicylaldiminato)platinum(II) complexes. Solutions of the clothespin-shaped platinum(II) complexes anti-1a–c in cyclohexane immediately transformed into stable gels upon brief ultrasound irradiation. The ultrasound gels exhibited intense phosphorescent emissions at room temperature, whereas none of the solution exhibited significant emissions under UV light illumination. Interestingly, gels prepared from optically pure complexes exhibited CPL activity at room temperature with an anisotropy factor of |g_lum| = 1.5–2.6 × 10^-3. The emissive gels were readily converted to the original non-emissive solution upon heating and cooling to room temperature and could be gelled again by ultrasound irradiation. In addition, chromogenic control from green to red emission can be achieved simply by introducing MeO groups at different positions on the aromatic rings.

Keywords

circularly polarized luminescence / phosphorescence / platinum complex / supramolecular gel / ultrasound

References

[1] J. P. Riehl, F. S. Richardson, Chem. Rev. 1986, 86, 1.

[2] F. Zinna, L. Di Bari, Chirality 2015, 27, 1.

[3] E. M. Sánchez-Carnerero, A. R. Agarrabeitia, F. Moreno, B. L. Maroto, G. Muller, M. J. Ortiz, S. de La Moya, Chem. Eur J. 2015, 21, 13488.

[4] J. Kumar, T. Nakashima, T. Kawai, J. Phys. Chem. Lett. 2015, 6, 3345.

[5] N. Chen, B. Yan, Molecules 2018, 23, 3376.

[6] D.-Y. Kim, J. Korean Phys. Soc. 2006, 49, S505.

[7] C. Wagenknecht, C.-M. Li, A. Reingruber, X.-H. Bao, A. Goebel, Y.-A. Chen, Q. Zhang, K. Chen, J.-W. Pan, Nat. Photonics 2010, 4, 549.

[8] a) Y. Inoue, Chem. Rev. 1992, 92, 741.b) R. D. Richardson, M. G. J. Baud, C. E. Weston, H. S. Rzepa, M. K. Kuimova, M. J. Fuchter, Chem. Sci. 2015, 6, 3853.

[9] a) H. Maeda, Y. Bando, Pure Appl. Chem. 2013, 85, 1967.b) J.-L. Ma, Q. Peng, C.-H. Zhao, Chem. Eur J. 2019, 25, 15441.c) Y. Gao, C. Ren, X. Lin, T. He, Front. Chem. 2020, 8, 458. d) Y. Imai, Chem. Lett. 2021, 50, 1131.e) J. Liu, Z.-P. Song, L.-Y. Sun, B.-X. Li, Y.-Q. Lu, Q. Li, Responsive Mater. 2023, 1, e20230005.

[10] a) H. Maeda, Y. Bando, K. Shimomura, I. Yamada, M. Naito, K. Nobusawa, H. Tsumatori, T. Kawai, J. Am. Chem. Soc. 2011, 133, 9266.b) A. Mart-Lasanta, L. Álvarez de Cienfuegos, A. Johnson, D. Miguel, A. J. Mota, A. Orte, M. J Ruedas-Rama, M. Ribagorda, D. J. Cárdendenas, M. C. Carreño, A. M. Echavarren, J. M. Cuerva, Chem. Sci. 2014, 5, 4582.c) Y. Nagata, T. Nishikawa, M. Suginome, Chem. Commun. 2014, 50, 9951.d) H. Isla, M. Srebro-Hooper, M. Jean, N. Vanthuyne, T. Roisnel, J. L. Lunkley, G. Muller, J. A. Gareth Williams, J. Autschbach, J. Crassous, Chem. Commun. 2016, 52, 5932.e) S. P. Morcillo, D. Miguel, L. Álvarez de Cienfuegos, J. Justicia, S. Abbate, E. Castiglioni, C. Bour, M. Ribagorda, D. J. Cárdemas, J. M. Paredes, L. Crovetto, D. C. Lazarte, A. J. Mota, M. C. Carreño, G. Longhi, J. M. Cuerva, Chem. Sci. 2016, 7, 5663.f) T. Otani, A. Tsuyuki, T. Iwachi, S. Someya, K. Tateno, H. Kawai, T. Saito, K. S. Kanyiva, T. Shibata, Angew. Chem., Int. Ed. 2017, 56, 3906.g) P. Reiné, A. M. Ortuño, S. Resa, L. Álvarez de Cienfuegos, V. Blanco, M. J Ruedas-Rama, G. Mazzeo, S. Abbated, A. Lucotti, M. Tommasini, S. Guisán-Ceinos, M. Ribagorda, A. G. Campaña, A. Mota, G. Longhi, D. Miguel, J. M. Cuerva, Chem. Commun. 2018, 54, 13985.h) K. Takaishi, M. Yasui, T. Ema, J. Am. Chem. Soc. 2018, 140, 5334.i) A. H. G. David, R. Casares, J. M. Cuerva, A. G. Campaña, V. Blanco, J. Am. Chem. Soc. 2019, 141, 18064.j) E. Yen-Pon, F. Buttard, L. Frédéric, P. Thuéry, F. Taran, G. Pieters, P. A. Campagne, D. Audidio, JACS Au 2021, 1, 807.k) M. Ikeshita, H. He, M. Kitahara, Y. Imai, T. Tsuno, RSC Adv. 2022, 12, 34790.l) M. Ikeshita, Y. Tani, M. Kitahara, Y. Imai, T. Tsuno, Bull. Chem. Soc. Jpn. 2023, 96, 969.

[11] a) J. Kumar, T. Nakashima, T. Kawai, Langmuir 2014, 30, 6030.b) Q. Ye, D. Zhu, H. Zhang, X. Lu, Q. Lu, J. Mater. Chem. C 2015, 3, 6997.c) F. Song, Y. Cheng, Q. Liu, Z. Qiu, J. W. Y. Lam, L. Lin, F. Yang, B. Z. Tang, Mater. Chem. Front. 2019, 3, 1768.d) Z.-B. Sun, J.-K. Liu, D.-F. Yuan, Z.-H. Zhao, X.-Z. Zhu, D.-H. Liu, Q. Peng, C.-H. Zhao, Angew. Chem., Int. Ed. 2019, 58, 4840. e) G. Namba, Y. Mimura, Y. Imai, R. Inoue, Y. Morisaki, Chem. Eur J. 2020, 26, 14871.

[12] a) K. Okano, M. Taguchi, M. Fujiki, T. Yamashita, Angew. Chem., Int. Ed. 2011, 50, 12474.b) M. Louis, R. Sethy, J. Kumar, S. Katao, R. Guillot, T. Nakashima, C. Allain, T. Kawai, R. Métivier, Chem. Sci. 2019, 10, 843.c) T. Maeda, T. Mori, M. Ikeshita, S. C. Ma, G. Muller, K. Ariga, T. Naota, Small Methods 2022, 6, 2200936.

[13] a) H. Hayasaka, T. Miyashita, K. Tamura, K. Akagi, Adv. Funct. Mater. 2010, 20, 1243.b) A. Gopal, M. Hifsudheen, S. Furumi, M. Takeuchi, A. Ajayaghosh, Angew. Chem., Int. Ed. 2012, 51, 10505.c) Y. Hashimoto, T. Nakashima, D. Shimizu, T. Y. Kawai, Chem. Commun. 2016, 52, 5171.d) H. Li, H. Li, W. Wang, Y. Tao, S. Wang, Q. Yang, Y. Jiang, C. Zheng, W. Huang, R. Chen, Angew. Chem., Int. Ed. 2020, 59, 4756.e) J.-G. Yang, K. Li, J. Wang, S. Sun, W. Chi, C. Wang, X. Chang, C. Zou, W.-P. To, M.-D. Li, X. Liu, W. Lu, H.-X. Zhang, C.-M. Che, Y. Chen, Angew. Chem., Int. Ed. 2020, 59, 6915.f) M. Li, Y. Zhou, J. Li, W. Huang, Z. Yao, Y. Li, T. Gao, P. Yan, H. Li, Chin. Chem. Lett. 2024, 35, 108831.

[14] a) D. H. Metcalf, T. C. VanCott, S. W. Snyder, P. N. Schatz, B. E. Williamson, J. Phys. Chem. 1990, 94, 2828.b) Y. Imai, ChemPhotoChem 2021, 5, 969.c) K. Matsudaira, Y. Mimura, J. Hotei, S. Yagi, K.-i. Yamashita, M. Fujiki, Y. Imai, Chem. Asian J. 2021, 16, 926.d) K. Hara, A. Morimoto, K. Matsudaira, S. Suzuki, S. Yagi, M. Fujiki, Y. Imai, ChemPhotoChem 2022, 6, e202100253. e) F. Zinna, G. Pescitelli, Eur. J. Org. Chem. 2023, 26, e202300509.

[15] a) G. Cravotto, P. Cintas, Chem. Soc. Rev. 2009, 38, 2684.b) X. Yu, L. Chen, M. Z. T. Yi, Chem. Soc. Rev. 2014, 43, 5346.

[16] a) X. Yan, F. Wang, B. Zheng, F. Huang, Chem. Soc. Rev. 2012, 41, 6042.b) X. He, J. Fan, K. L. Wooley, Chem. Asian J. 2016, 11, 437.c) C. D. Jones, J. W. Steed, Chem. Soc. Rev. 2016, 45, 6546.d) D. Han, J. Wang, T. Zheng, L. Peng, T. Jiao, Cell Rep. Phys. Sci. 2023, 4, 101523.e) X.-F. Hou, X. Chen, J.-H. Wei, Y. Xu, X.-M. Chen, Q. Li, Responsive Mater. 2023, 1, e20230016.

[17] K. Fu, G. Liu, Chem. Commun. 2023, 59, 13751.

[18] M. Ikeshita, N. Hara, Y. Imai, T. Naota, Inorg. Chem. 2023, 62, 13964.

[19] M. Ikeshita, S. C. Ma, G. Muller, T. Naota, Dalton Trans. 2024, 53, 7775.

[20] a) T. Naota, H. Koori, J. Am. Chem. Soc. 2005, 127, 9324.b) N. Komiya, T. Muraoka, M. Iida, M. Miyanaga, K. Takahashi, T. Naota, J. Am. Chem. Soc. 2011, 133, 16054.c) M. Naito, R. Inoue, M. Iida, Y. Kuwajima, S. Kawamorita, N. Komiya, T. Naota, Chem. Eur. J. 2015, 21, 12927.

[21] M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid PlotProgram for Crystal Structure Illustrations, Report ORNL-6895, Oak Ridge National Laboratory, Oak Ridge 1996.

[22] M. Ikeshita, M. Ito, T. Naota, Eur. J. Inorg. Chem. 2019, 2019, 3561.

[23] M. D. Luque de Castro, F. Priego-Capote, Ultrason. Sonochem. 2007, 14, 717.

[24] K. S. Suslick, D. A. Hammerton, R. E. Cline, Jr., J. Am. Chem. Soc. 1986, 108, 5641.

[25] Q. Evrard, F. Houard, C. Daiguebonne, G. Calvez, Y. Suffren, O. Guillou, M. Mannini, K. Bernot, Inorg. Chem. 2020, 59, 9215.

[26] L. Rosenfeld, Z. Phys. 1929, 52, 161.

[27] H. Tanaka, Y. Inoue, T. Mori, ChemPhotoChem 2018, 2, 386.

[28] F. P. Fanizzi, F. P. Intini, L. Maresca, G. Natile, J. Chem. Soc. Dalton Trans. 1990, 199.

[29] A. D. Becke, in Modern Electronic Structure Theory, Part II (D. R. Yarkony, Ed.), World Scientific, Singapore 1995.

[30] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, GAUSSIAN 09 (Revision A.02), Gaussian, Inc., Wallingford, CT 2009.

[31] a) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270.b) P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299.

[32] a) M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654.b) P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213.

[33] a) M. E. Casida, C. Jamorski, K. C. Casida, D. R. Salahub, J. Chem. Phys. 1998, 108, 4439.b) R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218.

RIGHTS & PERMISSIONS

2024 The Author(s). Responsive Materials published by John Wiley & Sons Australia, Ltd on behalf of Southeast University.