Comparison of One-/Two-photon Absorption Properties of D-A-D Type Zinc Phthalocyanines Constructed with Different Rylene Diimides

doi:10.1007/s40242-025-5130-9

Abstract

Abstract: As a bulky conjugated molecule, phthalocyanine is commonly combined with rylene diimides acceptors to form novel organic optical functional dyes with better planarity and conjugation, which has led to a wide range of applications in photovoltaic conversion, photodynamic therapy and photocatalysis. In this paper, we have compared the one-photon absorption (OPA) and two-photon absorption (TPA) properties of D-A-D structural zinc phthalocyanine donors constructed with different rylene diimides acceptors [naphthalene diimide (NDI), perylene diimide (PDI) and terrylene diimide (TDI)] based on time-dependent density functional theory (TD-DFT) and sum-over-states (SOS) method. With the addition of NDI, PDI and TDI groups as the acceptors, new absorption peaks can appear in the OPA spectra and the absorption spectral range can be expanded. Meanwhile, the increase of naphthalene ring contributes to the expansion of TPA cross-section and the appearance of stronger charge transfer characteristics in the TPA spectra, which will be confirmed in the transition density matrix (TDM) and charge density difference (CDD) diagrams.

Key words: Zinc phthalocyanine, Rylene diimide, Two-photon absorption, Density functional theory

ZHANG Ding, WANG Yaochuan, NI Haoran, SUN Xue, WANG Yizhuo, LIU Dajun, XU Xuesong, CHEN Yu. Comparison of One-/Two-photon Absorption Properties of D-A-D Type Zinc Phthalocyanines Constructed with Different Rylene Diimides[J]. Chemical Research in Chinese Universities, 2026, 42(2): 612-621.

References

[1] Gandarias I., García-Fernández S., Obregón I., Agirrezabal-Telleria I., Arias P. L., Fuel Process. Technol., 2018, 178, 336.
[2] Kulkarni B. B., Maradur S. P., Bioresour. Technol., 2024, 402, 130805.
[3] Giorgianni G., Perathoner S., Centi G., Soo-Tang S. H., de Jong E., van der Waal J. C., Abate S., Chem. Eng. Res. Des., 2023, 197, 968.
[4] Li B., Li L., Sun H., Zhao C., ACS Sustainable Chem. Eng., 2018, 6, 12096.
[5] Gilkey M. J., Panagiotopoulou P., Mironenko A. V., Jenness G. R., Vlachos D. G., Xu B., ACS Catal., 2015, 5, 3988.
[6] Wang C., Wei L., Cheng Z., Xu H., Daniel R., Shuai S., Combust. Sci. Technol., 2015, 188, 329.
[7] Banerjee D., Sahu A. K., Clegg J. K., Upadhyayula S., Chem. Eng. J., 2024, 493, 152552.
[8] Yao C., Hou Y., Wu W., Ren S., Liu H., Green Chemistry, 2018, 20, 3101.
[9] Aghel B., Mohadesi M., Gouran A., Sep. Sci. Technol., 2019, 55, 3402.
[10] Warrag S. E. E., Darwish A. S., Adeyemi I. A., Hadj-Kali M. K., Kroon M. C., AlNashef I. M., Fluid Phase Equilib., 2020, 517, 112622.
[11] Yu Y., Zhang L., Zhu C., Huang X., Liao Z., Li Q., J. Solution Chem., 2020, 49, 1.
[12] Zhu Z., Xu Y., Feng T., Wang N., Liu K., Fan H., Reyes-Labarta J. A., Wang Y., Gao J., Wang L., J. Mol. Liq., 2020, 298, 111947.
[13] Casás L. M., Orge B., Ferreira O., J. Chem. Eng. Data, 2008, 53, 89.
[14] da Silva J. L., Aznar M., Fuel, 2014, 136, 316.
[15] Dai F., He G., Xin K., Shi M., Li J., Li Q., J. Chem. Thermodyn., 2017, 115, 91.
[16] Li C., Wang X., Li H., Duan C., An L., Liu Q., J. Chem. Eng. Data., 2019, 64, 1780.
[17] Yu Y., Zhang X., Yi L., Li M., Zhang F., Wei J., J. Chem. Eng. Data., 2022, 67, 1195.
[18] Renon H., Prausnitz J. M., AlChE J., 1968, 14, 135.
[19] Zhang Y., Li H., Li H., Shan R., Zhu Z., Wang Y., Gao J., J. Chem. Thermodyn., 2022, 167, 106715.
[20] Ding Y., Guo Y., Sun Y., Sun T., Ye Q., Li J., Paricaud P., Peng C., Ind. Eng. Chem. Res., 2022, 61, 16193.
[21] Boys S. F., Bernardi F., Mol. Phys., 1970, 19, 553.
[22] Lu T., Chen F., J. Comput. Chem., 2011, 33, 580.
[23] Humphrey W. A. D., Schulten K., J. Mol. Graph., 1996, 14, 33.
[24] Fu Y., Song X., Pang Y., Zheng Y., Gao L., J. Mol. Struct., 2023, 1290, 136000.
[25] Martínez L., Andrade R., Birgin E. G., Martínez J. M., J. Comput. Chem., 2009, 30, 2157.
[26] Berendsen H. J. C., van der Spoel D., van Drunen R., Comput. Phys. Commun., 1995, 91, 43.
[27] Fan W., Ge C., Ding D., Deng L., Gao J., Xu D., J. Chem. Thermodyn., 2023, 182, 107036.
[28] Zhang A., Yan H., Niu X., Han M., Wang W., Zhang Z., Lu W., Li T., Li Q., J. Chem. Eng. Data., 2023, 68, 2645.
[29] Araya-López C., Contreras J., Merlet G., Cabezas R., Olea F., Villarroel E., Salazar R., Romero J., Quijada-Maldonado E., Fluid Phase Equilib., 2022, 561, 113518
[30] Chen X., Gao X., Zheng H., Zhao S., Wang L. E., Fluid Phase Equilib., 2012, 313, 102.
[31] Sun C., Xing J., Qu Y., Zhang Y., Cui P., Wang Y., Gao J., Ind. Eng. Chem. Res., 2023, 62, 9302.
[32] Wang W., Wang Y., Lu W., Zhao W., Zhu Z., Cui P., Li X., Song X., Sep. Purif. Technol., 2025, 359, 130587.