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Theoretical study of the electronic ground states and low-lying singlet excited states of thiophene-based spirofluorenes

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  • Multiscale Modeling & Simulation of Materials
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Abstract

The electronic structures and optical properties of oligothiophene substituted spirofluorenes are investigated theoretically with semi-empirical quantum chemical calculations. A theoretical investigation of the interaction between two perpendicular π-systems of various oligothiophene substituted spirofluorenes is conducted. The results demonstrate that the interaction between two perpendicular branches is reduced by oligothiophene substitutions. Photoexcitation induced relaxation is mainly located on one of the equivalent branches or the branch with longer conjugation length. In addition to these benefits brought by 9,9-spirobifluorene center, the specific oligothiophene moieties linked to the spiro center also have properties of significant merit, such as the ability to tune energy levels and emission colors by controlling the conjugation length.

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References

  1. Saragi T P, Spehr T, Siebert A, et al. Spiro compounds for organic optoelectronics. Chem Rev, 2007, 107: 1011–1065; Xie L H, Liang J, Song J, et al. Spirocyclic aromatic hydrocarbons (SAHs) and their synthetic methodologies. Curr Org Chem, 2010, 18: 2169–2195

    Article  Google Scholar 

  2. Zeng G, Yu W L, Chua S J, et al. Spectral and thermal spectral sta bility study for fluorene-based conjugated polymers. Macromolecules, 2002, 35: 6907–6914; Chen R F, Zhu R, Zheng C, et al. Germafluorene conjugated copolymer: Synthesis and applications in blue-light-emitting diodes and host materials. Sci Chin Ser B-Chem, 2009, 52: 212–218

    Article  ADS  Google Scholar 

  3. Heeger A J. Semiconducting polymers: The third generation. Chem Soc Rev, 2010, 39: 2354–2371

    Article  Google Scholar 

  4. Yu W L, Pei J, Huang W, et al. Spiro-functionalized polyfluorene derivatives as blue light-emitting materials. Adv Mat, 2000, 12: 828–831

    Article  Google Scholar 

  5. Xie L H, Hou X Y, Tang C, et al. Novel H-shaped persistent architecture based on a dispirlo building block system. Org Lett, 2006, 8: 1363–1366

    Article  Google Scholar 

  6. Dewar M J S, Thiel W. Ground states of molecules. 38. The MNDO method. Approximations and parameters. J Am Chem Soc, 1977, 99: 4899–4907

    Article  Google Scholar 

  7. Hyperchem Release 4.5. Hypercube, Inc., 1995

  8. AMPAC Version 6.51, Semichem, 7128, Shawnee, KS 66216, 1997

  9. Ridley J E, Zerner M C. Triplet states via intermediate neglect of differential overlap: Benzene, pyridine and the diazines. Theor Chim Acta, 1976, 42: 223–236

    Article  Google Scholar 

  10. Yin J, Chen R F, Zhang S, et al. Theoretical studies of the structural, electronic, and optical properties of phosphafluorenes. J Phys Chem A, 2010, 114: 3655–3667

    Article  Google Scholar 

  11. Chen R F, Zheng C, Fan Q L, et al. Structural, electronic, and optical properties of 9-heterofluorenes: A quantum chemical study. J Comput Chem, 2007, 28: 2091–2101

    Article  Google Scholar 

  12. Schweig A, Weidner U, Hellwinkel D, et al. Spiroconjugation. Angew Chem Int Ed, 1973, 12: 310–311

    Article  Google Scholar 

  13. Johansson N, Santos dos D A, Guo S, et al. Electronic structure and optical properties of electroluminescent spiro-type molecules. J Chem Phys, 1997, 107: 2542–2549

    Article  ADS  Google Scholar 

  14. Cornil J, Beljonne D, Heller C M, et al. Photoluminescence spectra of oligo-paraphenylenevinylenes: A joint theoretical and experimental characterization. Chem Phys Lett, 1997, 278: 139–145; Yin J, Zhang S L, Chen R F, et al. Carbazole endcapped heterofluorenes as host materials: Theoretical study of their structural, electronic, and optical properties. Phys Chem Chem Phys, 2010, 12: 15448–15458

    Article  ADS  Google Scholar 

  15. Chen R F, Pan J, Zhang Y, et al. Theoretical investigation of the tunable behavior of p-n copolymers based on oligothiophenes and 1,4-Bis(oxadiazolyl)-benzene. J Phys Chem B, 2006, 110: 23750–23755

    Article  Google Scholar 

  16. Simmons H E, Fukunaga T. Spiroconjucation. J Am Chem Soc, 1967, 89: 5208–5215; Jang S E, Joo C W, Jeon S O, et al. The relationship between the substitution position of the diphenylphosphine oxide on the spirobifluorene and device performances of blue phosphorescent organic light-emitting diodes. Org Electron, 2010, 11: 1059–1065

    Article  Google Scholar 

  17. Ni J. The Design, Synthesis, and Characterization of Thiophene-functionalized Light-emitting Materials. Dissertation for Master Degree. Singapore: National University of Singapore, 2001

    Google Scholar 

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Authors and Affiliations

  1. Key Laboratory for Organic Electronics & Information Displays, Institute of Advanced Materials, Nanjing University of Posts & Telecommunications, Nanjing, 210046, China

    RunFeng Chen, Cong Ma, JingFang Pan, Chao Zheng & Wei Huang

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  1. RunFeng Chen
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  2. Cong Ma
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  3. JingFang Pan
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  4. Chao Zheng
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  5. Wei Huang
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Correspondence to Wei Huang.

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Chen, R., Ma, C., Pan, J. et al. Theoretical study of the electronic ground states and low-lying singlet excited states of thiophene-based spirofluorenes. Sci. China Phys. Mech. Astron. 54, 884–889 (2011). https://doi.org/10.1007/s11433-011-4318-9

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  • DOI: https://doi.org/10.1007/s11433-011-4318-9

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