Photoinduced excimer generation in perylene diimide dimer: effects of solvent polarity [Invited]

Guangliu Ran; Hang Wang; Yujing Song; Yahui Liu; Zhishan Bo; Wenkai Zhang

doi:10.3788/COL202220.100009

[1] N. A. Bumagina, E. V. Antina, A. A. Ksenofontov, L. A. Antina, A. A. Kalyagin, M. B. Berezin. Basic structural modifications for improving the practical properties of BODIPY. Coord. Chem. Rev., 469, 214684(2022).

[2] S. Silvestri, A. R. Fajardo, B. A. Iglesias. Supported porphyrins for the photocatalytic degradation of organic contaminants in water: a review. Environ. Chem. Lett., 20, 731(2022).

[3] P. Murugan, T. Hu, X. Hu, Y. Chen. Advancements in organic small molecule hole-transporting materials for perovskite solar cells: past and future. J. Mater. Chem. A, 10, 5044(2022).

[4] A. K. Mitra. Sesquicentennial birth anniversary of carbazole, a multifaceted wonder molecule: a revisit to its synthesis, photophysical and biological studies. J. Iran. Chem. Soc., 19, 2075(2022).

[5] M. Ciganek, J. Richtar, M. Weiter, J. Krajcovic. Organic π-conjugated molecules: from nature to artificial applications. where are the boundaries?. Isr. J. Chem., 62, e202100061(2022).

[6] D. Barman, K. Narang, R. Parui, N. Zehra, M. N. Khatun, L. R. Adil, P. K. Iyer. Review on recent trends and prospects in π-conjugated luminescent aggregates for biomedical applications. Aggregate, e172(2022).

[7] L. Luo, W. Huang, C. Yang, J. Zhang, Q. Zhang. Recent advances on pi-conjugated polymers as active elements in high performance organic field-effect transistors. Front. Phys., 16, 33500(2021).

[8] Y. Hino, T. Matsuo, S. Hayashi. Structural phase transitions in anthracene crystals. Chempluschem, 87, e202200157(2022).

[9] L. Zhang, Z. Chen, F. Sun, Y. Wang, H. Bao, X. Gao, Z. Liu. Progress of monomeric perylene diimide derivatives as non-fullerene acceptors for organic solar cells. J. Electron. Mater., 51, 4224(2022).

[10] C. Lin, T. Kim, J. D. Schultz, R. M. Young, M. R. Wasielewski. Accelerating symmetry-breaking charge separation in a perylenediimide trimer through a vibronically coherent dimer intermediate. Nat. Chem., 14, 786(2022).

[11] G. Ran, J. Zeb, Y. Song, P. A. Denis, U. Ghani, W. Zhang. Photoinduced symmetry breaking-charge separation in the aggregated state of perylene diimide: effect of hydrophobicity. J. Phys. Chem. C, 126, 3872(2022).

[12] E. Sebastian, M. Hariharan. Symmetry-breaking charge separation in molecular constructs for efficient light energy conversion. ACS Energy Lett., 7, 696(2022).

[13] M. Son, K. H. Park, C. Shao, F. Wuerthner, D. Kim. Spectroscopic demonstration of exciton dynamics and excimer formation in a sterically controlled perylene bisimide dimer aggregate. J. Phys. Chem. Lett., 5, 3601(2014).

[14] K. E. Brown, W. A. Salamant, L. E. Shoer, R. M. Young, M. R. Wasielewski. Direct observation of ultrafast excimer formation in covalent perylenediimide dimers using near-infrared transient absorption spectroscopy. J. Phys. Chem. Lett., 5, 2588(2014).

[15] W. Kim, A. Nowak-Krol, Y. Hong, F. Schlosser, F. Wuerthner, D. Kim. Solvent-modulated charge-transfer resonance enhancement in the excimer state of a bay-substituted perylene bisimide cyclophane. J. Phys. Chem. Lett., 10, 1919(2019).

[16] Y. Hong, J. Kim, W. Kim, C. Kaufmann, H. Kim, F. Wuerthner, D. Kim. Efficient multiexciton state generation in charge-transfer-coupled perylene bisimide dimers via structural control. J. Am. Chem. Soc., 142, 7845(2020).

[17] H. Wang, M. Li, Y. Liu, J. Song, C. Li, Z. Bo. Perylene diimide based star-shaped small molecular acceptors for high efficiency organic solar cells. J. Mater. Chem. C, 7, 819(2019).

[18] G. Ran, J. Zeb, H. Lu, Y. Liu, A. Zhang, L. Wang, Z. Bo, W. Zhang. Ultrafast carrier dynamics of non-fullerene acceptors with different planarity: impact of steric hindrance. J. Phys. Chem. Lett., 13, 5860(2022).

[19] A. T. R. Williams, S. A. Winfield, J. N. Miller. Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer. Analyst, 108, 1067(1983).

[20] X. Xu, A. Austin, S. E. Mylon, J. Plenge, J. M. Szarko. Improving the quantum yields of perylene diimide aggregates by increasing molecular hydrophobicity in polar media. ChemPhysChem, 18, 2430(2017).

[21] S. Kang, T. Kim, Y. Hong, F. Wuerthner, D. Kim. Charge-delocalized state and coherent vibrational dynamics in rigid PBI H-aggregates. J. Am. Chem. Soc., 143, 9825(2021).

[22] Z. Chen, B. Fimmel, F. Wuerthner. Solvent and substituent effects on aggregation constants of perylene bisimide π-stacks: a linear free energy relationship analysis. Org. Biomol. Chem., 10, 5845(2012).

[23] M. R. Islam, P. R. Sundararajan. Self-assembly of a set of hydrophilic-solvophobic-hydrophobic coil-rod-coil molecules based on perylene diimide. Phys. Chem. Chem. Phys., 15, 21058(2013).

[24] C. Kaufmann, W. Kim, A. Nowak-Krol, Y. Hong, D. Kim, F. Wuerthner. Ultrafast exciton delocalization, localization, and excimer formation dynamics in a highly defined perylene bisimide quadruple pi-stack. J. Am. Chem. Soc., 140, 4253(2018).

[25] J. Kong, W. Zhang, G. Li, D. Huo, Y. Guo, X. Niu, Y. Wan, B. Tang, A. Xia. Excited-state symmetry-breaking charge separation dynamics in multibranched perylene diimide molecules. J. Phys. Chem. Lett., 11, 10329(2020).

[26] F. Wuerthner. Solvent effects in supramolecular chemistry: linear free energy relationships for common intermolecular interactions. J. Org. Chem., 87, 1602(2022).

[27] J. Sung, P. Kim, B. Fimmel, F. Wuerthner, D. Kim. Direct observation of ultrafast coherent exciton dynamics in helical pi-stacks of self-assembled perylene bisimides. Nat. Commun., 6, 8646(2015).

[28] I. Solymosi, S. Krishna, E. Nuin, H. Maid, B. Scholz, D. M. Guldi, M. E. Perez-Ojeda, A. Hirsch. Diastereoselective formation of homochiral flexible perylene bisimide cyclophanes and their hybrids with fullerenes. Chem. Sci., 12, 15491(2021).

[29] Y. Y. Guo, Z. T. Ma, X. M. Niu, W. Zhang, M. Tao, Q. J. Guo, Z. H. Wang, A. D. Xia. Bridge-mediated charge separation in isomeric N-annulated perylene diimide dimers. J. Am. Chem. Soc., 141, 12789(2019).

[30] J. Sung, A. Nowak-Krol, F. Schlosser, B. Fimmel, W. Kim, D. Kim, F. Wuerthner. Direct observation of excimer-mediated intramolecular electron transfer in a cofacially-stacked perylene bisimide pair. J. Am. Chem. Soc., 138, 9029(2016).

[31] E. Sebastian, M. Hariharan. Null exciton-coupled chromophoric dimer exhibits symmetry-breaking charge separation. J. Am. Chem. Soc., 143, 13769(2021).

[32] C. E. Ramirez, S. Chen, N. E. Powers-Riggs, I. Schlesinger, R. M. Young, M. R. Wasielewski. Symmetry-breaking charge separation in the solid state: tetra(phenoxy)perylenediimide polycrystalline films. J. Am. Chem. Soc., 142, 18243(2020).

Data from CrossRef