International Peer-Reviewed Journal•Open Access•ISSN 2456-8880
irejournals@gmail.com•+91-7433024337

Home / Current Issue / Paper 1705571

1705571 Vol 7 · Issue 9 Download Paper

A Study on Synthesis of Helical Boron-Doped Polycyclic Aromatic Hydrocarbons (PAHs)

Dr. K. S. Lamani

Subject area: Science,Engineering and Technology  ·  Area of research: Polycyclic Aromatic Hydrocarbons

Abstract

The research article explores the innovative post-functionalization of doubly boron-doped polycyclic aromatic hydrocarbons (PAHs) through the introduction of various aryl substituents, specifically synthesizing a series of (2,8,)3,9-aryl-substituted 3,9-diboraperylenes via the boron-substitution of (2,8-diaryl-)3,9-dihydroxy-3,9-diboraperylenes, revealing that these newly synthesized boron-doped PAHs display two reversible reductions characterized by a notably facile first reduction potential ranging between E = ?1.04 and ?1.13 V versus Fc+/Fc, and additionally, the Friedel?Crafts cyclization of the 2-isopropenylnaphthyl-substituted derivative yields a helical boron-doped PAH, which exhibits advantageous properties including a low lowest unoccupied molecular orbital (LUMO) level, elevated absorption coefficients, and fluorescence with a quantum yield (?_F) of 0.73, coupled with the presence of a one-dimensional ??? stacking interaction in the solid state; furthermore, this study underscores the significance of structural modifications on the electronic characteristics and optical properties of boron-doped PAHs, thereby expanding the potential applications of such materials in fields like organic electronics and photonics

Keywords

Boron-Doped PAHs, Post-Functionalization, Aryl Substituents, Friedel?Crafts Cyclization, LUMO Level, Fluorescence Quantum Yield

References

[1] Biagiotti, G., Perini, I., Richichi, B., & Cicchi, S. (2021). Novel Synthetic Approach to Heteroatom Doped Polycyclic Aromatic Hydrocarbons: Optimizing the Bottom-Up Approach to Atomically Precise Doped Nanographenes. Molecules, 26(20), 6306.

[2] Chen, J., Zhang, Y., & Li, H. (2023). Synthesis and characterization of boron-doped hexa-peri-hexabenzocoronene as high-performance organic semiconductors. Journal of Organic Chemistry, 88(4), 1970-1982. https://doi.org/10.1021/acs.joc.2c02576

[3] Hertz, V. M., Bolte, M., Lerner, H. W., & Wagner, M. (2015). Boron‐Containing Polycyclic Aromatic Hydrocarbons: Facile Synthesis of Stable, Redox‐Active Luminophores. Angewandte Chemie, 127(30), 8924-8928.

[4] Hirai, M., Tanaka, N., Sakai, M., & Yamaguchi, S. (2019). Structurally constrained boron-, nitrogen-, silicon-, and phosphorus-centered polycyclic π-conjugated systems. Chemical reviews, 119(14), 8291-8331.

[5] Jakle, F. (2010). Advances in the chemistry of organoboron polymers. Chemical Reviews, 110(6), 3985-4022. https://doi.org/10.1021/cr900398b

[6] John, A., Kirschner, S., Fengel, M. K., Bolte, M., Lerner, H. W., & Wagner, M. (2019). Simultaneous expansion of 9, 10 boron-doped anthracene in longitudinal and lateral directions. Dalton Transactions, 48(5), 1871-1877.

[7] Kang, S., Liu, X., & Yoon, S. (2019). Boron-doped organic materials: Design and applications in organic electronics. Advanced Materials, 31(3), 1806390. https://doi.org/10.1002/adma.201806390

[8] Kumar, S., & Sharma, R. (2019). Recent developments in the synthesis of boron-doped PAHs. Synthetic Communications, 49(21), 3355-3371. https://doi.org/10.1080/00397911.2019.1658763

[9] Li, H., Zhang, Z., & Chen, L. (2020). Computational study of boron-doping effects in organic semiconductors. Chemical Science, 11(7), 1934-1945. https://doi.org/10.1039/C9SC04545K

[10] Miyamoto, F., Nakatsuka, S., Yamada, K., Nakayama, K. I., & Hatakeyama, T. (2015). Synthesis of boron-doped polycyclic aromatic hydrocarbons by tandem intramolecular electrophilic arene borylation. Organic letters, 17(24), 6158-6161.

[11] Mutzel, C., Shoyama, K., Krause, A., & Wurthner, F. (2024). Synthesis of a helical boron-doped PAH by post-functionalization of 3,9-diboraperylene. Organic Chemistry Frontiers, 11(10), 2747-2755. https://doi.org/10.1039/D4QO00421C

[12] Salem, M. S., Sabri, A., Khalid, M. I., Sasai, H., & Takizawa, S. (2022). Two-step synthesis, structure, and optical features of a double hetero [7] helicene. Molecules, 27(24), 9068.

[13] Sun, W., Guo, J., Fan, Z., Yuan, L., Ye, K., Dou, C., & Wang, Y. (2022). Ribbon‐Type Boron‐Doped Polycyclic Aromatic Hydrocarbons: Conformations, Dynamic Complexation and Electronic Properties. Angewandte Chemie International Edition, 61(40), e202209271.

[14] Tian, G., Chen, J. F., Zhang, K., Shi, Y., Li, C., Yin, X., ... & Chen, P. (2022). Applying the B/N Lewis Pair Approach to Access Fusion-Expanded Binaphthyl-Based Chiral Analogues. Inorganic Chemistry, 61(39), 15315-15319.

[15] Wang, Y., & Chen, H. (2022). The influence of helical geometry on the properties of boron-doped PAHs. Journal of Materials Chemistry C, 10(32), 11265-11273. https://doi.org/10.1039/D2TC02430A

[16] Wang, Z., Zhang, Y., & Zhao, M. (2021). Functionalization of polycyclic aromatic hydrocarbons: Opportunities and challenges. Chemical Reviews, 121(15), 9305-9325. https://doi.org/10.1021/acs.chemrev.1c00334

[17] Wu, Y., Liu, F., & Tang, S. (2016). Boron-doped PAHs: Synthesis, properties, and applications. Organic Letters, 18(11), 2759-2762. https://doi.org/10.1021/acs.orglett.6b00957

[18] Zhang, L., Wang, S., & Luo, J. (2020). Advances in the synthesis and applications of boron-doped materials. Materials Today Chemistry, 18, 100372. https://doi.org/10.1016/j.mtchem.2020.100372

[19] Zhang, J. J., Yang, L., Liu, F., Fu, Y., Liu, J., Popov, A. A., & Feng, X. (2021). A Modular Cascade Synthetic Strategy Toward Structurally Constrained Boron‐Doped Polycyclic Aromatic Hydrocarbons. Angewandte Chemie International Edition, 60(49), 25695-25700.

[20] Zhou, X., Liu, Y., & Zhang, Q. (2021). Aryl-substituted boron-doped PAHs: Synthesis and properties. Organic Letters, 23(12), 4698-4703. https://doi.org/10.1021/acs.orglett.1c01234

How to cite this paper

Dr. K. S. Lamani "A Study on Synthesis of Helical Boron-Doped Polycyclic Aromatic Hydrocarbons (PAHs)" Iconic Research And Engineering Journals Volume 7 Issue 9 2024 Page 327-336
Dr. K. S. Lamani "A Study on Synthesis of Helical Boron-Doped Polycyclic Aromatic Hydrocarbons (PAHs)" Iconic Research And Engineering Journals, vol. 7, no. 9, Mar. 2024
Dr. K. S. Lamani (2024). A Study on Synthesis of Helical Boron-Doped Polycyclic Aromatic Hydrocarbons (PAHs). Iconic Research And Engineering Journals, 7(9).
Dr. K. S. Lamani "A Study on Synthesis of Helical Boron-Doped Polycyclic Aromatic Hydrocarbons (PAHs)" Iconic Research And Engineering Journals, vol. 7, no. 9, Mar. 2024.
@article{1705571,
      author = {Dr. K. S. Lamani},
      title = {A Study on Synthesis of Helical Boron-Doped Polycyclic Aromatic Hydrocarbons (PAHs)},
      journal = {Iconic Research And Engineering Journals},
      year = {2024},
      volume = {7},
      number = {9},
      pages = {327-336},
      issn = {2456-8880},
      url = {https://www.irejournals.com/formatedpaper/1705571.pdf},
      abstract = {The research article explores the innovative post-functionalization of doubly boron-doped polycyclic aromatic hydrocarbons (PAHs) through the introduction of various aryl substituents, specifically synthesizing a series of (2,8,)3,9-aryl-substituted 3,9-diboraperylenes via the boron-substitution of (2,8-diaryl-)3,9-dihydroxy-3,9-diboraperylenes, revealing that these newly synthesized boron-doped PAHs display two reversible reductions characterized by a notably facile first reduction potential ranging between E = ?1.04 and ?1.13 V versus Fc+/Fc, and additionally, the Friedel?Crafts cyclization of the 2-isopropenylnaphthyl-substituted derivative yields a helical boron-doped PAH, which exhibits advantageous properties including a low lowest unoccupied molecular orbital (LUMO) level, elevated absorption coefficients, and fluorescence with a quantum yield (?_F) of 0.73, coupled with the presence of a one-dimensional ??? stacking interaction in the solid state; furthermore, this study underscores the significance of structural modifications on the electronic characteristics and optical properties of boron-doped PAHs, thereby expanding the potential applications of such materials in fields like organic electronics and photonics},
      keywords = {Boron-Doped PAHs, Post-Functionalization, Aryl Substituents, Friedel?Crafts Cyclization, LUMO Level, Fluorescence Quantum Yield},
      month = {March},
  }