Skip to main content
SpringerLink
Log in

Synthesis of phthalocyanines with donor–acceptor properties and their applications to dye-sensitized solar cell

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

In this study, photovoltaic cell devices based on phthalocyanine structures with metal-free and zinc metal-containing D–π–A substitutes consisting of biphenyl and cyano-containing substituents have been synthesized. The non-symmetrical phthalocyanine photo-sensitizer has three biphenyls and one cyano group, respectively, which act as electron release and withdrawal. The new light-sensitive dye cells were tested in dye-sensitive solar cells and the performance was compared to N719 dye. All compounds synthesized were characterized using FTIR, 1 H NMR, C NMR, UV–Vis and MS spectroscopic data. First, the relationship between symmetric and non-symmetric ZnPc and H2Pc morphology and photovoltaic properties was discussed. The effects of symmetric and asymmetric cyano groups on solar cell efficiency were investigated. Furthermore, according to the results from the non-symmetrical ZnPc device prepared at room temperature, it was determined that it exhibited relatively higher photovoltaic cell efficiency due to significant improvements in short-circuit photo-current (Jsc) and open-circuit voltage (Voc).

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Schema 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Ali HEA, Altındal A, Altun S, Odabaş Z (2016) Highly efficient dye-sensitized solar cells based on metal-free and copper (II) phthalocyanine bering 2-phenylphenoxy moiety. Dyes Pigments 124:180–187

    Article  CAS  Google Scholar 

  • Erdoğmuş A, Nyokong T (2009) New soluble methylendioxy-phenoxy-substituted zinc phthalocyanine derivatives: synthesis, photo physical and photochemical studies. Polyhedron 28(14):2855–2862

    Article  CAS  Google Scholar 

  • Grätzel M (2003) Dye-sensitized solar cells. J Photochem Photobiol C 4(2):145–153

    Article  CAS  Google Scholar 

  • Hu L, Dai S, Weng J, Xiao S, Sui Y, Huang Y, Wang K (2007) Microstructure design of nanoporous TiO2 photoelectrodes for dye-sensitized solar cell modules. J Phys Chem B 111(2):358–362

    Article  CAS  PubMed  Google Scholar 

  • Jono R, Fujisawa JI, Segawa H, Yamashita K (2011) Theoretical study of the surface complex between TiO2 and TCNQ showing interfacial charge-transfer transitions. J Phys Chem Lett 2(10):1167–1170

    Article  CAS  PubMed  Google Scholar 

  • Kalkan A, Bayır ZA (2006) Phthalocyanines with rigid carboxylic acid containing pendant arms. Polyhedron 25(1):39–42

    Article  CAS  Google Scholar 

  • Kamat PV (1993) Photochemistry on nonreactive and reactive (semiconductor) surfaces. Chem Rev 93(1):267–300

    Article  CAS  Google Scholar 

  • Kanaparthi RK, Kandhadi J, Giribabu L (2012) Metal-free organic dyes for dye-sensitized solar cells: recent advances. Tetrahedron 68(40):8383–8393

    Article  CAS  Google Scholar 

  • Kao PC, Chu SY, Liu SJ, You ZX, Chuang CA (2006) Improved performance of organic light-emitting diodes using a metal-phthalocyanine hole-injection layer. J Electrochem Soc 153(6):H122–H126

    Article  CAS  Google Scholar 

  • Kay A, Graetzel M (1993) Artificial photosynthesis. 1. Photosensitization of titania solar cells with chlorophyll derivatives and related natural porphyrins. J Phys Chem 97(23):6272–6277

    Article  CAS  Google Scholar 

  • Kim BH, Freeman HS (2013) New N-methyl pyrrole and thiophene based D–π–A systems for dye-sensitized solar cells. Dyes Pigments 96(2):313–318

    Article  CAS  Google Scholar 

  • Kim S, Kim D, Choi H, Kang MS, Song K, Kang SO, Ko J (2008) Enhanced photovoltaic performance and long-term stability of quasi-solid-state dye-sensitized solar cells via molecular engineering. Chem Commun 40:4951–4953

    Article  CAS  Google Scholar 

  • Mao J, He N, Ning Z, Zhang Q, Guo F, Chen L, Tian H (2012) Stable dyes containing double acceptors without COOH as Anchors for highly efficient dye-sensitized solar cells. Angew Chem Int Ed 51(39):9873–9876

    Article  CAS  Google Scholar 

  • Mao J, Wang D, Liu SH, Hang Y, Xu Y, Zhang Q, Hua J (2014) Dye-sensitized solar cells based on functionally separated D–π–A dyes with 2-cyanopyridine as an electron-accepting and anchoring group. Asian J Org Chem 3(2):153–160

    Article  CAS  Google Scholar 

  • Michinobu T, Satoh N, Cai J, Li Y, Han L (2014) Novel design of organic donor–acceptor dyes without carboxylic acid anchoring groups for dye-sensitized solar cells. J Mater Chem C 2(17):3367–3372

    Article  CAS  Google Scholar 

  • Nazeeruddin MK, Splivallo R, Liska P, Comte P, Grätzel M (2003) A swift dye uptake procedure for dye sensitized solar cells. Chem Commun 12:1456–1457

    Article  Google Scholar 

  • O’regan B, Grätzel M (1991) A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 353(6346):737

    Article  Google Scholar 

  • Smestad GP (1998) Education and solar conversion: demonstrating electron transfer. Sol Energy Mater Sol Cells 55(1–2):157–178

    Article  CAS  Google Scholar 

  • Song JL, Amaladass P, Wen SH, Pasunooti KK, Li A, Yu YL, Liu XW (2011) Aryl/hetero-arylethyne bridged dyes: the effect of planar π-bridge on the performance of dye-sensitized solar cells. New J Chem 35(1):127–136

    Article  CAS  Google Scholar 

  • Wang L, Liang M, Zhang Y, Cheng F, Wang X, Sun Z, Xue S (2014) Influence of donor and bridge structure in D–A–π–A indoline dyes on the photovoltaic properties of dye-sensitized solar cells employing iodine/cobalt electrolyte. Dyes Pigments 101:270–279

    Article  CAS  Google Scholar 

  • Wu Y, Zhu W (2013) Organic sensitizers from D–π–A to D–A–π–A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances. Chem Soc Rev 42(5):2039–2058

    Article  PubMed  Google Scholar 

  • Wu G, Kong F, Li J, Chen W, Fang X, Zhang C, Dai S (2013) Influence of different acceptor groups in julolidine-based organic dye-sensitized solar cells. Dyes Pigments 99(3):653–660

    Article  CAS  Google Scholar 

  • Yanagisawa M, Korodi F, Bergquist J, Holmberg A, Hagfeldt A, Åkermark B, Sun L (2004) Synthesis of phthalocyanines with two carboxylic acid groups and their utilization in solar cells based on nano-structured TiO 2. J Porphyr Phthalocyanines 8(10):1228–1235

    Article  CAS  Google Scholar 

  • Zhang L, Cole JM (2015) Anchoring groups for dye-sensitized solar cells. ACS Appl Mater Interfaces 7(6):3427–3455

    Article  CAS  PubMed  Google Scholar 

  • Zhang J, Kan YH, Li HB, Geng Y, Wu Y, Su ZM (2012) How to design proper π–spacer order of the D–π–A dyes for DSSCs? A density functional response. Dyes Pigments 95(2):313–321

    Article  CAS  Google Scholar 

  • Zhou R, Josse F, Göpel W, Öztürk ZZ, Bekaroğlu Ö (1996) Phthalocyanines as sensitive materials for chemical sensors. Appl Organomet Chem 10(8):557–577

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Yildiz Technical University, 34220, Istanbul, Turkey

    B. Karadoğan, F. Aytan Kılıçarslan & I. Erden

Authors
  1. B. Karadoğan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. F. Aytan Kılıçarslan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. Erden
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. Karadoğan.

Additional information

Publisher's Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 4276 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karadoğan, B., Kılıçarslan, F.A. & Erden, I. Synthesis of phthalocyanines with donor–acceptor properties and their applications to dye-sensitized solar cell. Chem. Pap. 73, 2283–2288 (2019). https://doi.org/10.1007/s11696-019-00778-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-019-00778-x

Keywords

Search

Navigation