Photoinduced Bending and Curling Motions in Molecular Microcrystals of Naphthyl Meldrum's Acid Derivative Based on E-to-Z Photoisomerization

doi:10.1007/s40242-024-4153-y

Chemical Research in Chinese Universities ›› 2024, Vol. 40 ›› Issue (5): 907-913.doi: 10.1007/s40242-024-4153-y

• Articles • Previous Articles Next Articles

Photoinduced Bending and Curling Motions in Molecular Microcrystals of Naphthyl Meldrum's Acid Derivative Based on E-to-Z Photoisomerization

ZHANG Xiaowen, XU Tianyi, ZHANG Chenchen, TONG Fei

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P. R. China

Received:2024-06-30 Online:2024-10-01 Published:2024-09-26
Contact: TONG Fei,feitong@ecust.edu.cn E-mail:feitong@ecust.edu.cn
Supported by:
This work was supported by the National Natural Science Foundation of China (Nos.22105071,22375063),the Project of the Science and Technology Commission of Shanghai Municipality,China (Nos.22ZR1417100,23JC1401700),and the Fundamental Research Funds for the Central Universities,China (No.B16017).

Abstract

Abstract: Dynamic photoresponsive molecular crystals are promising candidates for making intelligent devices and materials in the future. Here, we synthesized a new photoactive molecule (E)-2,2-dimethyl-5-[3-(naphthalen-1-yl) allylide]-1,3-dioxane-4,6-dione [(E)-DNADD] that undergoes an E-to-Z photoisomerization in both liquid solution and solids when exposed to visible light (405 nm). Compared to the bulk crystals, the photoresponsive behavior in microcrystals was profoundly improved. Highly crystalline (E)-DNADD microplate crystals exhibit robust motions, including bending, curling, and coiling under light irradiation. The photoproduct conversion of the photochemical reaction in the microplate is no more than 20%, while the large bending curvature of the coiled illuminated samples was estimated at approximately 150—300 mm^-1, comparable to some photoactive nanowires. Our results indicate that shrinking crystal dimensions can boost the photoresponses in molecular crystals and provide a facile strategy for developing dynamic molecular crystals at the microscopic scale.

Key words: Photochemistry, Molecular crystal, E-to-Z photoisomerization, Photoinduced motion

ZHANG Xiaowen, XU Tianyi, ZHANG Chenchen, TONG Fei. Photoinduced Bending and Curling Motions in Molecular Microcrystals of Naphthyl Meldrum's Acid Derivative Based on E-to-Z Photoisomerization[J]. Chemical Research in Chinese Universities, 2024, 40(5): 907-913.

References

[1] Yang M., Yuan Z., Liu J., Fang Z., Fang L., Yu D., Li Q., Adv. Opt. Mat., 2019, 7, 1900069.
[2] Yan J., Zheng Q., Wang S. P., Tian Y. Z., Gong W. Q., Gao F., Qiu J. J., Li L., Yang S. H., Cao M. S., Adv. Mater., 2023, 35, 2300015.
[3] Zeng J. Y., Wang X. S., Xie B. R., Li Q. R., Zhang X. Z., J. Am. Chem. Soc., 2022, 144, 1218.
[4] Diao Z. J., Liu S. Y., Wen H., Liu G. L., Yang T., Li J. J., Liu X. Q., Sun L. B., Angew. Chem. Int. Ed., 2023, 135, e202301739.
[5] Zhao X., Wang L. Y., Tang C. Y., Zha X. J., Liu Y., Su B. H., Ke K., Bao R. Y., Yang M. B., Yang W., ACS Nano, 2020, 14, 8793.
[6] Gao Y. Y., Yan C., Huang H. C., Yang T., Tian G., Xiong D., Chen N. J., Chu X., Zhong S., Deng W. L., Fang Y., Yang W. Q., Adv. Funct. Mater., 2020, 30, 1909603.
[7] Sagara Y., Yamane S., Mitani M., Weder C., Kato T., Adv. Mater., 2016, 28, 1073.
[8] Yu X. D., Chen L. M., Zhang M. M., Yi T., Chem. Soc. Rev., 2014, 43, 5346.
[9] Li N., Yu S. S., Zhao L., Zhang P. F, Wang Z. Q., Wei Z. T., Chen W. B., Xu X. H., Inorg. Chem., 2023, 62, 2024.
[10] Zhang Z. J., Chen X. J., Zhang H. J., Liu W. X., Zhu W., Zhu Y. F., Adv. Mater., 2020, 32, 1907746.
[11] Varghese S. S., Varghese S. H., Swaminathan S., Singh K. K., Mittal V., Electronics, 2015, 4, 651.
[12] Chen R., Chen X., Zhou Y., Lin T., Leng Y., Huang X., Xiong Y., ACS Nano, 2022, 16, 3351.
[13] Shcherbakov M. R., Neshev D. N., Hopkins B., Shorokhov A. S., Staude I., Melik-Gaykazyan E. V., Decker M., Ezhov A. A., Miroshnichenko A. E., Brener I., Fedyanin A. A., Kivshar Y. S., Nano Lett., 2014, 14, 6488.
[14] Gelebart A. H., Mulder D. J., Varga M., Konya A., Vantomme G., Meijer E. W., Selinger R. L. B., Broer D. J., Nature, 2017, 546, 632.
[15] Zhang B., Li H. G., Cheng J. X., Ye H. T., Sakhaei A. H., Yuan C., Rao P., Zhang Y. F., Chen Z., Wang R., He X. N., Liu J., Xiao R., Qu S. X., Ge Q., Adv. Mater., 2021, 33, 2101298.
[16] Goulet-Hanssens A., Eisenreich F., Hecht S., Adv. Mater., 2020, 32, 1905966.
[17] Wang B. H., Thukral A., Xie Z. Q., Liu L. M., Zhang X. N., Huang W., Yu X. G., Yu C. J., Marks T. J., Facchetti A., Nat. Commun., 2020, 11, 2405.
[18] Bhandary S., Beliš M., Kaczmarek A. M., Van Hecke K., J. Am. Chem. Soc., 2022, 144, 22051.
[19] Liang L. L., Yu R. L., Ong S. J. H., Yang Y., Zhang B. S., Ji G. B., Xu Z. C. J., ACS Nano, 2023, 17, 12409.
[20] White T. J., Broer D. J., Nat. Mater., 2015, 14, 1087.
[21] Pang X. L., Lv J. A., Zhu C. Y., Qi L., Yu Y. L., Adv. Mater., 2019, 31, 1904224.
[22] Gelebart A. H., Mulder D. J., Varga M., Konya A., Vantomme G., Meijer E. W., Selinger R. L. B., Broer D. J., Nature, 2017, 546, 7660.
[23] Schultzke S., Scheuring N., Puylaert P., Lehmann M., Staubitz A., Adv. Sci., 2023, 10, 2302692.
[24] Kim H. K., Wang X. S., Fujita Y., Sudo A., Nishida H., Fujii M., Endo T., Polymer, 2005, 46, 5879.
[25] Luo P. F., Xiang S. L., Li C., Zhu M. Q., J. Polym. Sci., 2021, 59, 2246.
[26] Chen Y. H., Yang J. J., Zhang X., Y. Feng Y., Zeng H., Wang L., Feng W., Mater. Horiz., 2021, 8, 728.
[27] Xu L., Zheng H., Xue F., Ji Q., Qiu C., Yan Q., Ding R., Zhao X., Hu Y., Peng Q., He X., Chem. Eng. J., 2023, 463, 142392.
[28] Han S. J., Tudi A., Zhang W. B, Hou X. L., Yang Z. H., Pan S. L., Angew. Chem. Int. Ed., 2023, 62, e202302025.
[29] Awad W. M., Davies D. W., Kitagawa D., Halabi J. M., Al-Handawi M. B., Tahir I., Tong F., Campillo-Alvarado G., Shtukenberg A. G., Alkhidir T., Hagiwara Y., Almehairbi M., Lan L. F., Hasebe S., Karothu D. P., Mohamed S., Koshima H., Kobatake S., Diao Y., Chandrasekar R., Zhang H. Y., Sun C. C., Bardeen C., Al-Kaysi R. O., Kahr B., Naumov P., Chem. Soc. Rev., 2023, 52, 3098.
[30] Abendroth J. M., Bushuyev O. S., Weiss P. S., Barrett C. J., ACS Nano, 2015, 9, 7746.
[31] Morimoto K., Kitagawa D., Tong F., Chalek K., Mueller L. J., Bardeen C. J., Kobatake S., Angew. Chem. Int. Ed., 2022, 61, e202114089.
[32] Tong F., Qu D. H., Langmuir, 2022, 38, 4793.
[33] Kim T., Zhu L., Mueller L. J., Bardeen C. J., CrystEngComm, 2012, 14, 7792.
[34] Taniguchi T., Asahi T., Koshima H., Crystals, 2019, 9. 437.
[35] Xu T.Y., Tong F., Xu H., Wang M.-Q., Tian H., Qu D. H., J. Am. Chem. Soc., 2022, 144, 6278.
[36] Zhu L. Y., Tong F., Zaghloul N., Baz O., Bardeen C. J., Al-Kaysi R. O., J. Mater. Chem. C, 2016, 4, 8245.
[37] Tong F., Chen S. L., Li Z. W., Liu M. Y., Al-Kaysi R. O., Mohideen U., Yin Y. D., Bardeen C. J., Angew. Chem. Int. Ed., 2019, 58, 15429.
[38] Xu T. Y., Cui M., Zhao C., Zhou S. W., Zhang T. L., Lin H. Y., Tong F., Qu D. H., CCS Chemistry, 2024, 6, 1071.
[39] Schmidt G. M. J., Pure Appl. Chem., 1971, 27, 647.
[40] Tong F., Kitagawa D., Dong X. N., Kobatake S., Bardeen C. J., Nanoscale, 2018, 10, 3393.

Photoinduced Bending and Curling Motions in Molecular Microcrystals of Naphthyl Meldrum's Acid Derivative Based on E-to-Z Photoisomerization

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 5

Recommended Articles

Metrics

Comments

[1]	ZHANG Shixue, ZHOU Shengqi, WU Hao, GUO Xingwei. Advancements and Prospects in Continuous Wave Time-resolved Electron Paramagnetic Resonance [J]. Chemical Research in Chinese Universities, 2024, 40(5): 798-805.
[2]	ZHANG Tingting, LUO Pan, LAI Can, LIU Zheyi, JIN Yan, WANG Fangjun. Catalyst-free Photochemical Bromination of Unprotected Aromatic Amino Acid Derivatives by Using a Rotating Ultraviolet Photoreactor [J]. Chemical Research in Chinese Universities, 2022, 38(2): 505-509.
[3]	PENG Fei, XUE Hong-hai, TANG Xiao-jian, KANG Chun-li, LI Lin-lin, LI Zhe. Comparison of Photochemical Reactions of m-Cresol in Aqueous Solution and in Ice [J]. Chemical Research in Chinese Universities, 2012, 28(1): 47-52.
[4]	MAJID Kowsar , AHMAD Siraj , MALIK Mukhtar Ahmad. Novel Photoinitiated Synthesis, Characterization, Thermal Kinetics, and Mechanism of Complex of Potassium Hexacyanoferrate with Imidazole [J]. Chemical Research in Chinese Universities, 2009, 25(2): 138-142.
[5]	Yu Hengtai, Shen Erzhong, Ye Yuanjie, Zhang Gang. A Theoretical Study of Photochemical Reaction for Synthesis of Thiirane [J]. Chemical Research in Chinese Universities, 1988, 4(3): 40-45.