Photoinduced isomerization mechanism of isatin N<sup>2</sup>-diphenylhydrazones molecular switch

Pang Xiao-Juan; Zhao Kai-Yue; He Hang-Yu; Zhang Ning-Bo; Jiang Chen-Wei

doi:10.7498/aps.73.20240461

Abstract

Hydrazone molecular switches have significant application value in supramolecular chemistry. A new type of hydrazone molecular switch, named isatin N²-diphenylhydrazone, has been synthesized. Owing to its cis-trans isomerization characteristics under visible light excitation, ease of synthesizing of derivatives, and sensitivity to external stimuli, it has important application value in the field of biochemistry. Because of its forward and backward visible light excitation characteristics, it is considered a class of compound that is very suitable for molecular switches, and it has a wide application value in fields such as biotechnology. In addition, the derivatives compound exhibits strong interactions with negative ions, which enhances its function as a molecular switch, making it a four-state molecular switch that can be achieved by a single molecule. However, the photo-induced isomerization mechanism of these new molecular switches is not yet clear, and whether there are novel phenomena in the isomerization process is also unknown. In this work, a semi empirical OM2/MRCI based trajectory surface hopping dynamics method is adopted to systematically study a photo induced isomerization mechanism based on the E-Z isomerization process of the isatin N²-diphenylhydrazones molecular switch. Optimization configuration and the average lifetime of the first excited S₁ state are obtained by using the semi-empirical OM2/MRCI method of molecular switch. It is found that the average lifetime of the S₁ excited state of the E-configuration molecular switch is about 107 fs, and the quantum yield of E-Z isomerization of the molecular switch is 16.01%. By calculating the photo induced isomerization process of the molecular switch, two different isomerization mechanisms of the molecular switch are identified. In addition to the traditional molecular switch isomerization mechanism revolving around the C=N bond, a new isomerization mechanism, i.e. the face-to-face twisting of the molecular switch rotor part is elucidated. By calculating the time-resolved fluorescence radiation spectrum, it is predicted that there may be a very fast fluorescence quenching phenomenon occurring in about 75 fs in the isomerization process, slightly faster than the S₁ average decay events (107 fs). The information about wavelength-resolved attenuation at different times is also calculated, which reflects the ultrafast fluorescence quenching process accompanied by fluorescence red shift, ranging from 2.1 × 10⁴ cm^–1 to 3.4 × 10⁴ cm^–1. By comparing the calculated fluorescence spectra with the average lifetime of excited states, the existence of “dark states” is proposed, and possible explanations for the existence of “dark states” are provided, and those “dark states” may be related to lower quantum yields. The research results can provide theoretical guidance for the design and application of new molecular switches. The ease of synthesis and sensitivity to external stimuli of its derivatives make those compounds extremely valuable in molecular switching and light measurement applications.

Keywords:

Authors and contacts

1.
School of Materials and Physics, China University of Mining & Technology, Xuzhou 221116, China
2.
School of Mines, China University of Mining & Technology, Xuzhou 221116, China
3.
Shaanxi Province Key Laboratory of Quantum Information and Quantum Optoelectronic Devices, Ministry of Education Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, School of Physics, Xi’an Jiaotong University, Xi’an 710049, China

Corresponding author: Zhao Kai-Yue, ts22180023a31@cumt.edu.cn

Funds: Project supported by the National Natural Science Foundation of China (Grant Nos. 12204532, 52174137), the Natural Science Foundation of Jiangsu Province, China (Grant No. BK20200648), the Key Academic Project of China University of Mining and Technology (Grant No. 2022WLXK16), the Research Start-up Funding of China University of Mining and Technology (Grant No. 102519047), and the Graduate Innovation Project of China University of Mining and Technology (Grant No. 2024WLJCRCZL284).

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References

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Cited By

图 1 新型分子开关E-Z异构机制图, 最优基态反应物　(a) E及产物(b) Z的S₀最优构型图, 所有相关原子序号均已标注

Figure 1. E-Z isomerization mechanism diagram of a novel molecular switch, the optimal configuration diagram of S₀ for the optimal ground state reactant (a) E and product (b) Z, with all relevant atomic numbers marked.

DownLoad: Full-Size Img PowerPoint

图 2 新型分子开关半经验 OM2/MRCI方法下优化的第一激发态S₁最优构型

Figure 2. Optimization of the optimal configuration of the first excited state S₁ under the semi-empirical OM2/MRCI method of the novel molecular switch.

DownLoad: Full-Size Img PowerPoint

图 3 电子在基态S₀和第一激发态S₁的态平均占据数随时间变化情况

Figure 3. The average occupancy of electrons in the ground state S₀ and the first excited state S₁ over time.

DownLoad: Full-Size Img PowerPoint

图 4 新型分子开关异构化过程中的键长的变化趋势图　(a), (b)扭转过程中C8—N17 与C2—C8, N17—N16的变化趋势; (c), (d)旋转过程中C8—N17 与C2—C8, N17—N16变化趋势

Figure 4. Trend chart of bond length changes during the isomerization process of the novel molecular switch: (a), (b) The changing trends of C8—N17 and C2—C8, N17—N16 during the twisting process; (c), (d) changes in C8—N17 and C2—C8, N17—N16 during rotation.

DownLoad: Full-Size Img PowerPoint

图 5 新型分子开关异构化过程中的二面角的变化趋势　(a), (b)扭转过程中C2—C8—N17—N16, C7—C8—N17—N16与C8—N17—N16—C33, C8—N17—N16—C18的变化趋势; (c), (d)旋转过程中C2—C8—N17—N16, C7—C8—N17—N16与C8—N17—N16—C33, C8—N17—N16—C18的变化趋势

Figure 5. The changing trend of dihedral angle during the isomerization process of the novel molecular switch: (a), (b) The changing trends of C2—C8—N17—N16, C7—C8—N17—N16, C8—N17—N16—C33, and C8—N17—N16—C18 during the twisting process; (c), (d) the changing trends of C2—C8—N17—N16, C7—C8—N17—N16, C8—N17—N16—C33, and C8—N17—N16—C18 during the rotation process.

DownLoad: Full-Size Img PowerPoint

图 6 激发态动力学的含时荧光辐射光谱　(a)随时间变化荧光辐射光谱; (b)不同时间下随波长变化的衰减信息

Figure 6. Time-dependent fluorescence emission spectra of excited state dynamics: (a) The time-resolved deconvoluted emission spectrum; (b) the wavelength-resolved decay information in different time.

DownLoad: Full-Size Img PowerPoint

DownLoad: Full-Size Img PowerPoint

map

[1]	Li R J, Mou B Z, Yamada M, Li W, Nakashima T, Kawai T 2024 Molecules 29 25 Google Scholar
[2]	Jago D, Gaschk E E, Koutsantonis G A 2023 Aust. J. Chem. 76 635 Google Scholar
[3]	Yu Z, Hecht S 2016 Chem. Commun. 52 6639 Google Scholar
[4]	Feringa B L, Van Delden R A, Koumura N, Geertsema E M 2000 Chem. Rev. 100 1789 Google Scholar
[5]	Rice A M, Martin C R, Galitskiy V A, Berseneva A A, Leith G A, Shustova N B 2020 Chem. Rev. 120 8790 Google Scholar
[6]	Zhang X Y, Hou L L, Samorì P 2016 Nat. Commun. 7 11118 Google Scholar
[7]	Alenazi M H, Mubarak A T, Abboud M 2024 Nanotechnol. Rev. 13 20240032 Google Scholar
[8]	Goulet-Hanssens A, Eisenreich F, Hecht S 2020 Adv. Mater. 32 1905966 Google Scholar
[9]	Pios S V, Gelin M F, Ullah A, Dral P O, Chen L 2024 J. Phys. Chem. Lett. 15 2325 Google Scholar
[10]	Conti I, Cerullo G, Nenov A, Garavelli M 2020 J. Am. Chem. Soc. 142 16117 Google Scholar
[11]	Towns A 2021 Phys. Sci. Rev. 6 477 Google Scholar
[12]	Cheng H B, Zhang S, Bai E, Cao X, Wang J, Qi J, Liu J, Zhao J, Zhang L, Yoon J 2022 Adv. Mater. 34 2108289 Google Scholar
[13]	Bertarelli C, Bianco A, Castagna R, Pariani G 2011 J. Photoch. Photobio. C 12 106 Google Scholar
[14]	Bléger D, Hecht S 2015 Angew. Chem. Int. Ed. 54 11338 Google Scholar
[15]	Shao B, Aprahamian I 2020 Chem 6 2162 Google Scholar
[16]	Van Dijken D J, KovaříčEk P, Ihrig S P, Hecht S 2015 J. Am. Chem. Soc. 137 14982 Google Scholar
[17]	Schnetz M, Meier J K, Rehwald C, Mertens C, Urbschat A, Tomat E, Akam E A, Baer P, Roos F C, Brüne B 2020 Cancers 12 530 Google Scholar
[18]	Ferreira I P, Piló E D, Recio-Despaigne A A, Da Silva J G, Ramos J P, Marques L B, Prazeres P H, Takahashi J A, Souza-Fagundes E M, Rocha W 2016 Bioorg. Med. Chem. 24 2988 Google Scholar
[19]	Vantomme G, Lehn J M 2014 Chem. Eur. J. 20 16188 Google Scholar
[20]	Vantomme G, Lehn J M 2013 Angew. Chem. Int. Edit. 52 3940 Google Scholar
[21]	Vantomme G, Jiang S M, Lehn J M 2015 J. Am. Chem. Soc. 137 3138 Google Scholar
[22]	Su X, Aprahamian I 2014 Chem. Soc. Rev. 43 1963 Google Scholar
[23]	Chaur M N, Collado D, Lehn J M 2011 Chem. Eur. J. 17 248 Google Scholar
[24]	Vantomme G, Jiang S, Lehn J M 2014 J. Am. Chem. Soc. 136 9509 Google Scholar
[25]	刘同力, 黄从树, 王晶晶, 梁宇, 谢志鹏, 庄海燕, 李九龙, 朱绪飞 2024 精细化工 https://doi.org/10.13550/j.jxhg.20230989 Liu T L, Huang C S, Wang J J, Liang Y, Xie Z P, Zhuang H Y, Li J L, Zhu X F 2024 Fine. Chem https://doi.org/ 10.13550/ j.jxhg.20230989
[26]	Siewertsen R, Neumann H, Buchheim-Stehn B, Herges R, Näther C, Renth F, Temps F 2009 J. Am. Chem. Soc. 131 15594 Google Scholar
[27]	Beharry A A, Sadovski O, Woolley G A 2011 J. Am. Chem. Soc. 133 19684 Google Scholar
[28]	Poloni C, Szymanski W, Hou L L, Browne W R, Feringa B L 2014 Chem. Eur. J. 20 946 Google Scholar
[29]	Zhang Z W, Yang W X, Zhang J J 2023 Chem. Ind. Eng. Prog 42 4058 [张志伟, 杨伟鑫, 张隽佶 2023 化工进展 42 4058]Google Scholar Zhang Z W, Yang W X, Zhang J J 2023 Chem. Ind. Eng. Prog 42 4058 Google Scholar
[30]	Ye H 2020 M. S. Thesie (Wuhan: Huazhong University of Science and Technology) [叶欢 2020 硕士学位论文(武汉: 华中科技大学)] Ye H 2020 M. S. Thesie (Wuhan: Huazhong University of Science and Technology)
[31]	Szymanski W, Beierle J M, Kistemaker H A, Velema W A, Feringa B L 2013 Chem. Rev. 113 6114 Google Scholar
[32]	Cigán M, Gáplovsky M, Jakusová K, Donovalová J, Horváth M, Filo J, Gáplovsky A 2015 RSC Adv. 5 62449 Google Scholar
[33]	Cigáň M, Jakusová K, Gáplovský M, Filo J, Donovalová J, Gáplovský A 2015 Photochem. Photobiol. Sci. 14 2064 Google Scholar
[34]	Tisovský P, Donovalová J, Kožíšek J, Horváth M, Gáplovský A 2022 J. Photochem. Photobiol. A Chem. 427 113827 Google Scholar
[35]	Seleem H S 2011 Chem. Cent. J. 5 8 Google Scholar
[36]	Šandrik R, Tisovský P, Csicsai K, Donovalová J, Gáplovský M, Sokolík R, Filo J, Gáplovský A 2019 Molecules 24 2668 Google Scholar
[37]	Liu H H, Chen Y 2009 J. Phys. Chem. A 113 5550 Google Scholar
[38]	Tochitsky I, Polosukhina A, Degtyar V E, Gallerani N, Smith C M, Friedman A, Van Gelder R N, Trauner D, Kaufer D, Kramer R H 2014 Neuron 81 800 Google Scholar
[39]	Van Herpt J T, Areephong J, Stuart M C, Browne W R, Feringa B L 2014 Chem. Eur. J. 20 1737 Google Scholar
[40]	Nakagawa T, Ubukata T, Yokoyama Y 2018 J. Photochem. Photobiol. C-Photochem. Rev. 34 152 Google Scholar
[41]	Kistemaker J C M, Stacko P, Roke D, Wolters A T, Heideman G H, Chang M C, Van Der Meulen P, Visser J, Otten E, Feringa B L 2017 J. Am. Chem. Soc. 139 9650 Google Scholar
[42]	Kistemaker J C M, Stacko P, Visser J, Feringa B L 2015 Nature Chemistry 7 890 Google Scholar
[43]	Thiel W 1981 J. Am. Chem. Soc. 103 1413 Google Scholar
[44]	Wang J, Durbeej B 2018 ChemistryOpen 7 583 Google Scholar
[45]	Ma J Z, Yang S J, Zhao D, Jiang C W, Lan Z G, Li F L 2022 Int. J. Mol. Sci. 23 3908 Google Scholar
[46]	Pang X J, He H Y, Zhao K Y, Zhang N B, Zhong Q J 2023 Chem. Phys. Lett. 819 140439 Google Scholar
[47]	Zhuang X H, Wang J, Lan Z G 2013 J. Phys. Chem. A 117 4785 Google Scholar
[48]	Pang X J, Cui X Y, Hu D P, Jiang C W, Zhao D, Lan Z G, Li F L 2017 J. Phys. Chem. A 121 1240 Google Scholar
[49]	Weber W, Thiel W 2000 Theor. Chem. Acc. 103 495 Google Scholar
[50]	Otte N, Scholten M, Thiel W 2007 J. Phys. Chem. A 111 5751 Google Scholar
[51]	Lan Z G, Lu Y, Weingart O, Thiel W 2012 J. Phys. Chem. A 116 1510 Google Scholar
[52]	Jin H, Liang M, Arzhantsev S, Li X, Maroncelli M 2010 J. Phys. Chem. B 114 7565 Google Scholar

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Photoinduced isomerization mechanism of isatin N²-diphenylhydrazones molecular switch

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Corresponding author: Zhao Kai-Yue, ts22180023a31@cumt.edu.cn

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Photoinduced isomerization mechanism of isatin N2-diphenylhydrazones molecular switch

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Corresponding author: Zhao Kai-Yue, ts22180023a31@cumt.edu.cn

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Photoinduced isomerization mechanism of isatin N²-diphenylhydrazones molecular switch