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Design of novel molecules with considerable optical properties based on polymer of BODIPY molecules

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Abstract

In this research, the BODIPY molecule was selected; and based on its structure, using a different number of BODIPY molecules connected to each other, novel oligomers with significant electrical and optical properties were designed. After structural optimization, the frequency analysis and cohesive energy calculations were done to ensure the oligomers’ stability. The electronic properties of the designed oligomers were studied; and it was shown that by increasing the numbers of BODIPY molecules in designed structures, their Eg was narrowed. Finally, it was shown that by increasing the numbers of BODIPY molecules in oligomers, a great improvement in optical properties such as increasing the number of absorption lines and intensity of them was observed. Among the designed oligomers, two di- and tri-BODIPY molecules have substantial optical properties with intense absorption lines in visible and near-infrared regions.

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References

  1. Benniston AC, Copley G (2009) Lighting the way ahead with boron dypiromethene (BODIPY) dyes. Phys Chem Chem Phys 11:4121–4131

    Article  Google Scholar 

  2. Awuahab SG, You Y (2012) Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy. RSC Adv 2:11169–11183

    Article  Google Scholar 

  3. Boens N, Leen V, Dehaen W (2012) Fluorescent indicators based on BODIPY. Chem Soc Rev 41:1130–1172

    Article  CAS  Google Scholar 

  4. Kowada T, Maeda H, Kikuchi K (2015) BODIPY-Based probes for the fluorescence imaging of biomolecules in living cells. Chem Soc Rev 44:4953–4972

    Article  CAS  Google Scholar 

  5. Kamkaew A, Lim SH, Lee HB, Voon Kiew L, Chung LY, Burgess K (2013) BODIPY dyes in photodynamic therapy. Chem Soc Rev 42:77–88

    Article  CAS  Google Scholar 

  6. Qin W, Baruah M, Stefan A, Van der Auweraer M, Boens N (2005) Photophysical properties of BODIPY-derived hydroxyaryl fluorescent pH probes in solution. Chemphyschem 6:2343–2351

    Article  CAS  Google Scholar 

  7. Frath D, Yarnell JE, Ulrich G, Castellano FN, Ziessel R (2013). ChemPhysChem 14:3348–3354

    Article  CAS  Google Scholar 

  8. Ulrich G, Barsella A, Boeglin A, Niu S, Ziessel R (2014). ChemPhysChem 15:2693–2700

    Article  CAS  Google Scholar 

  9. Agazzi ML, Durantini JE, Gsponer NS, Durantini AM, Bertolotti SG, Durantini EN (2019) Light-harvesting antenna and proton-activated photodynamic effect of a novel BODIPY−fullerene C60 dyad as potential antimicrobial agent. ChemPhysChem 20:1–17

    Article  Google Scholar 

  10. Kaya EN, Köksoy B, Yeşilot S, Durmuş M (2020) Purple silicon(IV) phthalocyanine axially substituted with BODIPY groups. Dyes Pigments 172:107867

    Article  CAS  Google Scholar 

  11. Liu Y, Yang L, Ma C, Tangb A (2020). Dyes Pigments 173:107981

    Article  CAS  Google Scholar 

  12. Ortiz A (2019) Triarylamine-BODIPY derivatives: a promising building block as hole transporting materials for efficient perovskite solar cells. Dyes Pigments 171:107690

    Article  CAS  Google Scholar 

  13. Tanja R, Ingo K, Sergey M (2020) Borisov, bright far-red emitting BODIPYs via extension with conjugated fluorene and carbazole motifs. Dyes Pigments 174:108037

    Article  Google Scholar 

  14. Xu T, Yan C, Wu Y, Yuan C, Shao X (2019) Decorating BODIPY with electron-rich unit THDTAP: an ICT-based fluorometric sensor toward peroxide, acid, and electrochemical stimuli. Dyes Pigments 168:235–247

    Article  CAS  Google Scholar 

  15. Lin Y, Yin J, Li X, Pan C, Kuang G (2019) Luminescent BODIPY-based porous organic polymer for CO2 adsorption. J Wuhan Univ Technol Mater Sci Ed 34:440–445

    Article  CAS  Google Scholar 

  16. Alemdaroglu FE, Alexander SC, Ji D, Prusty DK, Borsch M, Herrmann A (2009) Poly(BODIPY)s: a new class of tunable polymeric dyes. Macromolecules 42:6529–6536

    Article  CAS  Google Scholar 

  17. Sen CP, Goud VD, Shrestha RG, Shrestha LK, Arigab K, Valiyaveettila S (2016) BODIPY based hyperbranched conjugated polymers for detecting organic vapors. Polym Chem 7:4213–4422

    Article  CAS  Google Scholar 

  18. He T, Tang D, Lin C, Shen X, Lu C, Xu L, Gu Z, Xu Z, Qiu H, Zhang Q, Yin S (2017) Conjugated polymers containing BODIPY and fluorene units for sensitive detection of CN− ions: site-selective synthesis, photo-physical and electrochemical properties. Polymers 9:512

    Article  Google Scholar 

  19. Squeo BM, Gregoriou VG, Avgeropoulos A, Baysec S, Allard S, Scherf U, Chochos CL (2017) BODIPY-based polymeric dyes as emerging horizon materials for biological sensing and organic electronic applications. Prog Polym Sci 71:26–52

    Article  CAS  Google Scholar 

  20. Frisch M, Trucks G, Schlegel HB, Scuseria G, Robb M, Cheeseman J, Scalmani G, Barone V, Mennucci B, Petersson G (1998) (Revision A.9), Gaussian Inc, Pittsburgh

  21. Runge E, Gross EK (1984) Density-functional theory for time-dependent systems. Phys Rev Lett 52:997. https://doi.org/10.1103/PhysRevLett.52.997

    Article  CAS  Google Scholar 

  22. Gross E, Kohn W (1985) Local density-functional theory of frequency-dependent linear response. Phys Rev Lett 55:2850

    Article  CAS  Google Scholar 

  23. Casida ME, Jamorski C, CaBOsida KC, Salahub DR (1998) Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: characterization and correction of the time-dependent local density approximation ionization threshold. J Chem Phys 108:4439

    Article  CAS  Google Scholar 

  24. O'boyle NM, Tenderholt AL, Langner KM (2008) Synthetic, structural, photophysical and computational studies of -conjugated. J Comput Chem 29:839–845

    Article  CAS  Google Scholar 

  25. Chai JD, Head-Gordon M (2008) Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys Chem Chem Phys 10:6615–6620

    Article  CAS  Google Scholar 

  26. Chai JD, Head-Gordon M (2008) Systematic optimization of long-range corrected hybrid density functionals. J Chem Phys 128:084106

    Article  Google Scholar 

  27. Zhao Y, Truhlar DG (2006) The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of fouzr M06-class functionals and 12 other functionals. Theor Chem Accounts 120:215–241

    Article  Google Scholar 

  28. Li SS (2006) Semiconductor physical electronics. Springer, New York

    Book  Google Scholar 

Download references

Acknowledgments

We are grateful to Professor Seik Weng Ng for making his software (G98W) and hardware (machine time) facilities available.

Funding

The authors received financial support from the Research and Graduate Study Councils of Lorestan University.

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Authors and Affiliations

  1. Chemistry Department, Lorestan University, Khorramabad, Iran

    Masoomeh Mehrabpour, Hamid Reza Shamlouei & Homayoon Bahrami

Authors
  1. Masoomeh Mehrabpour
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  2. Hamid Reza Shamlouei
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  3. Homayoon Bahrami
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Correspondence to Hamid Reza Shamlouei.

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Mehrabpour, M., Shamlouei, H.R. & Bahrami, H. Design of novel molecules with considerable optical properties based on polymer of BODIPY molecules. J Mol Model 26, 306 (2020). https://doi.org/10.1007/s00894-020-04565-4

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  • DOI: https://doi.org/10.1007/s00894-020-04565-4

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