Skip to main content
Log in

Synthesis and Photophysical Study of [60]Fullerene-Maleimide Dyads

  • RAPID COMMUNICATION
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Novel [60]fullerene-maleimide dyads were synthesized by covalent linking of maleimide fluorophore to the [60]fullerene (C60) via Bingel reaction. The dyads were well characterized and studied for their absorption and emission properties. The fluorescence quenching of maleimide moiety by C60 was observed, indicating the intramolecular energy transfer from maleimide fluorophore to C60 moiety.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

References

  1. Hedley GJ, Ruseckas A, Samuel IDW (2016) Light harvesting for organic photovoltaics. Chem Rev 117:796–837

    Article  Google Scholar 

  2. Echegoyen L, Diederich F, Echegoyen LE (2000) Electrochemistry of fullerenes in fullerenes: chemistry, physics, and technology. Wiley, New York

    Google Scholar 

  3. Guldi DM, Asmus K, Hirsch A, Prato M (2000) Small reorganization energies in fullerenes. Am Inst Phys 58:58–62

    Google Scholar 

  4. Li CZ, Yip HL, Jen AK (2012) Functional fullerenes for organic photovoltaics. J Mater Chem 22:4161–4177

    Article  CAS  Google Scholar 

  5. Andrea CE, Espinoza IB, Ortiz A (2018) Novel BODIPY-C60 derivatives with tuned photophysical and electronacceptor properties: Isoxazolino[60] fullerene and pyrrolidino[60]fullerene. J Lumin 194:729–738

    Article  Google Scholar 

  6. Kristy LM, Jeremy NW, Holloway T, Niklas J, Oleg GP (2015) Electronic structure of fullerene acceptors in organic bulk-Heterojunctions: a combined EPR and DFT study. J Phys Chem Lett 6:4730–4735

    Article  Google Scholar 

  7. Liang H, Zhu RM, Qin J, Zhou XH (2013) Synthesis and properties of a new Coumarin functionalized Tetrathiafulvalene derivative. J Chin Chem Soc 60:573–578

    Article  Google Scholar 

  8. Haiying Z, Zhang LZ, Tian X, Chen J, Zhu C, Zheng Y (2012) Synthesis, Photophysical and electrochemical properties of amide-linked Phthalocyanine-fullerene dyad. Chin J Chem 30:1766–1770

    Article  Google Scholar 

  9. Liu Y, Zhao J (2012) Visible light-harvesting perylenebisimide–fullerene (C60) dyads with bidirectional “ping-pong” energy transfer as triplet photosensitizers for photooxidation of 1,5-dihydroxynaphthalene. Chem Comm 48:3751–3753

    Article  CAS  Google Scholar 

  10. Nascimento S, Brites MJ, Santos C, Gigante B, Fedorov A, Berberan-Santos MN (2006) Resonance energy transfer in new fullerene-Coumarin Diads. J Fluoresc 16:245–250

    Article  CAS  Google Scholar 

  11. Brites MJ, Santos C, Nascimento S, Gigante B, Luftmann H, Fedorov A, Berberan-Santos MN (2006) Synthesis and fluorescence properties of [60] and [70]fullerene–coumarin dyads: efficient dipole–dipole resonance energy transfer from coumarin to fullerene. New J Chem 30:1036–1045

    Article  CAS  Google Scholar 

  12. Guldi DM (2002) Fullerene-porphyrin architectures; photosynthetic antenna and reaction Centre models. Chem Soc Rev 31:22–36

    Article  CAS  Google Scholar 

  13. Sera N, Tokiwa H, Miyata N (1996) Mutagenicity of the fullerene C60 generated singlet oxygen dependent formation of lipid peroxides. Carcinogenisis 17:2163–2169

    Article  CAS  Google Scholar 

  14. Nakamura E, Isobe H (2003) Functionalized fullerenes in water. The first 10 years of their chemistry, biology, and Nanoscience. Acc Chem Res 36:807–815

    Article  CAS  Google Scholar 

  15. Yu C, Canteenwala T, El-Khouly ME, Araki Y, Chiang LY (2005) Efficiency of singlet oxygen production from self-assembled nanospheres of molecular micelle-like photosensitizers FC4S. J Mater Chem 15:1857–1864

    Article  CAS  Google Scholar 

  16. Segura JL, Martin N, Guldi DM (2005) Materials for organic solar cells: the C60/π-conjugated oligomer approach. Chem Soc Rev 34:31–47

    Article  CAS  Google Scholar 

  17. Guldi DM, Luo TD, Prato M, Dietel E, Hirsch A (2000) Photo induced electron transfer in multicomponent arrays of a π-stacked fullerene porphyrin dyad and diazabicyclooctane or a fulleropyrrolidine ligand. Chem Comm 375–376

  18. Roncali J (2005) Linear π-conjugated systems derivatized with C60-fullerene as molecular heterojunctions for organic photovoltaics. Chem Soc Rev 34:483–495

    Article  CAS  Google Scholar 

  19. Kand D, Kalle AM, Talukdar P (2013) Chromenoquinoline-based thiol probes: a study on the quencher position for controlling fluorescent Off–On characteristics. Org Biomol Chem 11:1691–1701

    Article  CAS  Google Scholar 

  20. Wu WC, Yeh CY, Chan LH, Chen CT (2002) Red organic light emitting diodes with non-doping amorphous red emitter. Adv Mater 14:1072–1075

    Article  CAS  Google Scholar 

  21. Chan LH, Leeb UD, Chen CT (2006) Achieving saturated red photoluminescence and electroluminescence with readily synthesized maleimide-arylamine copolymers. Tetrahedron 62:9541–9547

    Article  CAS  Google Scholar 

  22. Bingel C (1993) Cyclopropylation of fullerenes. Chem Ber 126:1957–1959

    Article  CAS  Google Scholar 

  23. Gosavi KS (2015) Synthesis of novel heterocycles and covalently bonded [60] fullerenyl heterocycles for biological and material application. Savitribai Phule University of Pune, Dissertation

    Google Scholar 

  24. Williams AR, Winfield S, Miller JN (1983) Relative fluorescence quantum yields sing a computer controlled luminescence spectrometer. Analyst 108:1067–1071

    Article  CAS  Google Scholar 

  25. Patil VS, Padalkar VS, Sekar N (2014) 2-Methyl-4-oxo-N-(4-oxo-2-phenyl substituted-1,3-thiazolidin-3-yl)-3,4-dihydroquinazoline-5-carboxamides-a new range of fluorescent whiteners: synthesis and photophysical characterization. J Fluoresc 24:1077–1086

    Article  Google Scholar 

  26. Sun YP (1997) in V. Ramamurthy and K. S. Schanze (Eds.), Molecular and supramolecular photochemistry, Marcel Dekker, New York, pp. 325-390

Download references

Acknowledgments

SVP and KSG thanks University Grants Commission, New Delhi for financial support under major research project [F.2-2/2011(SAP-II)] and award of junior research fellowship respectively. We thank authorities of Maratha Vidya Prasarak Samaj, Nashik and KTHM College for providing laboratory facilities.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kirankumar S. Gosavi.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

ESM 1

(DOCX 1272 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gosavi, K.S., Mahale, K.A. & Patil, S.V. Synthesis and Photophysical Study of [60]Fullerene-Maleimide Dyads. J Fluoresc 30, 223–228 (2020). https://doi.org/10.1007/s10895-020-02495-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-020-02495-1

Keywords

Navigation