Yıl 2021, Cilt 8 , Sayı 1, Sayfalar 311 - 320 2021-02-28

A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties

Hüsniye ARDİC ALİDAGİ [1] , Seda ÇETİNDERE [2]


In the present work, a novel highly conjugated pyrene-BODIPY (BODPhPy) with a D-A (donor-acceptor) skeleton small molecule was synthesized by Sonogashira cross-coupling reaction between 1-ethynylpyrene as a donor group (EthyPy) and BODIPY as an acceptor group (BrPh-BOD). The new compound was characterized by fourier transform-infrared (FT-IR), nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MALDI-TOF) and elemental analysis. The photophysical and electrochemical properties of the compound (BODPhPy) were investigated by UV-vis absorption, fluorescence emission spectroscopy, and cyclic voltammetry (CV) in dichloromethane. It was found from the optical and electrocemical measurements that the target compound has highest occupied molecular orbital energy level (EHOMO) of -5.70 eV, lowest unoccupied molecular orbital energy level (ELUMO) of -3.27 eV, and the band gap was calculated as 2.43 eV. In addition, theoretic computational studies was also carried out via density functional techniques (DFT) for investigation of molecular structure and energy levels of the compound. According to this results, the novel compound could be potential candidate for optoelectronic devices.
Pyrene, BODIPY, optoelectronic device
  • 1. Ward MD. Photo-induced electron and energy transfer in non-covalently bonded supramolecular assemblies. Chemical Society Reviews. 1997; 26:365-75.
  • 2. Balzani V, Bergamini G, Ceroni P. From the photochemistry of coordination compounds to light-powered nanoscale devices and machines. Coordination Chemistry Reviews. 2008; 252:2456-69.
  • 3. Guldi DM. Fullerene-porphyrin architectures; photosynthetic antenna and reaction center models. Chemical Society Reviews. 2002; 31:22-36. 4. Haugland RP. Handbook of Fluorescent Probes and Research Chemicals, 10th ed.; Molecular Probes: Eugene, OR, 2005.
  • 5. Thoresen LH, Kim H, Welch MB, Burghart A, Burgess K. Synthesis of 3,5-diaryl-4,4-difluro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes. Synlett. 1998; 1276–1278.
  • 6. Rurack K, Kollmannsberger M, Daub J. A highly efficient sensor molecule emitting in the near infrared (NIR): 3,5-distyryl-8-(p-dimethylaminophenyl)difluoroboradiaza-s-indacene. New Journal of Chemistry. 2001; 25: 289–292.
  • 7. Loudet A, Burgess K. BODIPY Dyes and Their Derivatives:  Syntheses and Spectroscopic Properties. Chemical Reviews. 2007; 107:4891–4932.
  • 8. Ulrich G, Ziessel R, Harriman A. The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed. Angewandte Chemie International Edition. 2008; 47: 1184–201. 9. Kowada T, Maeda H, Kikuchi K. BODIPY-based probes for the fluorescence imaging of biomolecules in living cells. Chemical Society Reviews. 2015; 44: 4953–972.
  • 10. Ho D, Ozdemir R, Kim H, Earmme T, Usta H, Kim C. BODIPY-Based Semiconducting Materials for Organic Bulk Heterojunction Photovoltaics and Thin-Film Transistors. ChemPlusChem. 2019; 84: 18–37.
  • 11. Winnik FM. Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media. Chemical Reviews. 1993; 93:587-614.
  • 12. Duhamel J. New insights in the study of pyrene excimer fluorescence to characterize macromolecules and their supramolecular assemblies in solution. Langmuir. 2012; 28:6527-38.
  • 13. Yeşilot S, Çoşut B, Ardıç Alidağı H, Hacıvelioğlu F, Altınbaş Özpınar G, Kılıç A. Intramolecular excimer formation in hexakis- (pyrenyloxy)cyclotriphosphazene: photophysical properties, crystal structure, and theoretical investigation. Dalton Transaction. 2014; 43: 3428–33.
  • 14. Lambert C, Ehbets J, Rausch D, Steeger M. Charge-Transfer Interactions in a Multichromophoric Hexaarylbenzene Containing Pyrene and Triarylamines. Journal of Organic Chemistry. 2012; 77: 6147–54.
  • 15. Merz J, Fink J, Friedrich A, Krummenacher I, Al Mamari HH, Lorenzen S, Haehnel M, Eichhorn A, Moos M, Holzapfel M, Braunschweig H, Lambert C, Steffen A, Ji L, Marder TB. Pyrene Molecular Orbital Shuffle—Controlling Excited State and Redox Properties by Changing the Nature of the Frontier Orbitals. Chemistry Europian Journal. 2017; 23:13164–80.
  • 16. Raytchev M, Pandurski E, Buchvarov I, Modrakowski C, Fiebig T. Bichromophoric Interactions and Time-Dependent Excited State Mixing in Pyrene Derivatives. A Femtosecond Broad-Band Pump−Probe Study. Journal of Physical Chemistry A. 2003; 107: 4592–600.
  • 17. Krebs N, Pugliesi I, Hauer J, Riedle E. Two-dimensional Fourier transform spectroscopy in the ultraviolet with sub-20 fs pump pulses and 250–720 nm supercontinuum probe. New Journal of Physics. 2013; 15: 085016.
  • 18. Rodriguez-Cordoba W, Sierra CA, Puentes CO, Lahti PM, Peon J. Photoinduced energy transfer in bichromophoric pyrene-PPV oligomer systems: the role of flexible donor-acceptor bridges. Journal of Physical Chemistry B. 2012; 116: 3490–503.
  • 19. Lee OP, Yiu AT, Beaujuge PM, Woo CH, Holcombe TW, Millstone JE, Douglas JD, Chen MS, Frechet JMJ. Efficient small molecule bulk heterojunction solar cells with high fill factors via pyrene-directed molecular self-assembly. Advanced Materials. 2011; 23: 5359–63.
  • 20. Oniwa K, Kikuchi H, Shimotani H, Ikeda S, Asao N, Yamamoto Y, Tanigaki K, Jin T. 2-Positional pyrene end-capped oligothiophenes for high performance organic field effect transistors. Chemical Communications. 2016; 52: 4800-03.
  • 21. Ardıç Alidağı H, Cosut B, Kılıc A, Yesilot S. Synthesis and spectral properties of a hexameric pyrene-fluorene chromophore based on cyclotriphosphazene. Polyhedron. 2014; 81: 436–41.
  • 22. Figueira-Duarte TM, Mullen K. Pyrene-based materials for organic electronics. Chemical Reviews. 2011; 111: 7260–314.
  • 23. Callaghan S, Filatov MA, Savoie H, Boyle RW, Senge MO. In vitro cytotoxicity of a library of BODIPYanthracene and -pyrene dyads for application in photodynamic therapy. Photochemical & Photobiological Sciences. 2019; 18: 495–504.
  • 24. Ziessel R, Goze C, Ulrich G, Cesario M, Retailleau P, Harriman A, Rostron JP. Intramolecular energy transfer in pyrene-BODIPY molecular dyads and triads. Chemistry A Europian Journal. 2005; 11: 7366-78.
  • 25. Yang Y, Zhang L, Gao C, Xu L, Bai S, Liu X. Pyrene-based BODIPY: synthesis, photophysics and lasing properties under UV-pumping radiation. RSC Advances. 2014; 4: 38119-23. 26. Fakis M, Beckwith JS, Seintis K, Martinou E, Nançoz C, Karakostas N, Petsalakis I, Pistolis G, Vauthey E. Energy transfer and charge separation Dynamics in photoexcited pyrene–bodipy molecular dyads. Physical Chemistry Chemical Physics. 2018; 20: 837-49.
  • 27. Porcu P, Vonlanthen M, González-Méndez I, Ruiu A, Rivera E. Design of Novel Pyrene-Bodipy Dyads: Synthesis, Characterization, Optical Properties, and FRET Studies. Molecules. 2018; 23: 2289.
  • 28. Matin MM, Chakraborty P, Alam MS, Islam MM, Hanee U. Novel mannopyranoside esters as sterol 14α- demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies. Carbohydrate Research. 2020; 496: 108130.
  • 29. Özkınalı S, Çavuş MS, Sakin B. Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes. Journal of the Turkish Chemical Society Section A: Chemistry. 2018; 5(1): 159-78.
  • 30. Matin MM, Bhattacharjee SC, Chakraborty P, Alam MS. Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters. Carbohydrate Research. 2019; 485: 107812.
  • 31. Bernhardt S, Kastler M, Enkelmann V, Baumgarten M, and Müllen K. Pyrene as Chromophore and Electrophore: Encapsulation in a Rigid Polyphenylene Shell. Chemistry A Europian Journal. 2006; 12: 6117 – 28.
  • 32. Sun J, Zhong F, Yi X, Zhao J. Efficient Enhancement of the Visible-Light Absorption of Cyclometalated Ir(III) Complexes Triplet Photosensitizers with Bodipy and Applications in Photooxidation and Triplet−Triplet Annihilation Upconversion. Inorganic Chemistry. 2013; 52: 6299−6310.
  • 33. Çetindere S, Tümay SO, Şenocak A, Kılıç A, Durmuş M, Demirbaş E, Yeşilot S. Novel pyrene-BODIPY dyes based on cyclotriphosphazene scaffolds: Synthesis, photophysical and spectroelectrochemical properties. Inorganica Chimica Acta. 2019; 494: 132–40.
  • 34. Cosut B. Highly efficient energy transfer in BODIPY-pyrene decorated cyclotriphosphazene. Dyes and Pigments. 2014; 100:11–16.
  • 35. Cetindere S. Photophysics of BODIPY Dyes: Recent Advances. Intech Open. Chapter, 2020.
  • 36. Mahapatra AK, Maji R, Maiti K, Manna SK, Mondal S, Ali SS, Manna S, Sahoo P, Mandal S, Uddin MR, Mandal D. A BODIPY/pyrene-based chemodosimetric fluorescent chemosensor for selective sensing of hydrazine in the gas and aqueous solution state and its imaging in living cells. RSC Advances. 2015; 5: 58228–36.
  • 37. Karolin J, Johansson LBA, Strandberg L, Ny T. Fluorescence and Absorption Spectroscopic Properties of Dipyrrometheneboron Difluoride (BODIPY) Derivatives in Liquids, Lipid Membranes, and Proteins. Journal of American Chemical Society. 1994; 116: 7801-6.
  • 38. Toele P, Zhang H, Trieflinger C, Daub J, Glasbeek M. Femtosecond fluorescence upconversion study of a boron dipyrromethene dye in solution. Chemical Physics Letters. 2003; 368: 66-75.
  • 39. Harriman A, Hissler M, Ziessel R. Photophysical properties of pyrene-(2,2′-bipyridine) dyads. Physical Chemistry Chemical Physics. 1999; 1: 4203-11.
  • 40. Zhou XF. 4,4-Difluoro-1,3,5,7-tetra­methyl-8-penta­fluoro­phenyl-4-bora-3a,4a-diaza-s-indacene. Acta Crystallographica Section E. 2010; E66: o757.
  • 41. Dobkowski J, Rettig W, Waluk J. Intramolecular Charge- Transfer Properties of a Molecule with a Large Donor Group: The Case of 4′-(Pyren-1-yl)Benzonitrile. Physical Chemistry Chemical Physics. 2002; 4: 4334−9.
  • 42. Soultati A, Verykios A, Panagiotakis S, Armadorou KK, Haider MI, Kaltzoglou A, Drivas C, Fakharuddin A, Bao X, Yang C, Rashid bin Mohd Yusoff A, Evangelou EK, Petsalakis I, Kennou S, Falaras P, Yannakopoulou K, Pistolis G, Argitis P, Vasilopoulou M. Suppressing the Photocatalytic Activity of Zinc Oxide Electron-Transport Layer in Nonfullerene Organic Solar Cells with a Pyrene-Bodipy Interlayer. ACS Applied Materials & Interfaces. 2020; 12(19): 21961−73.
Birincil Dil en
Konular Kimya, Organik
Bölüm Makaleler
Yazarlar

Orcid: 0000-0002-8446-4560
Yazar: Hüsniye ARDİC ALİDAGİ (Sorumlu Yazar)
Kurum: GEBZE TECHNICAL UNIVERSITY
Ülke: Turkey


Orcid: 0000-0001-7599-8491
Yazar: Seda ÇETİNDERE
Kurum: GEBZE TECHNICAL UNIVERSITY
Ülke: Turkey


Teşekkür It is our pleasure to present this study consisting of selected papers based on poster presentations from the 2020 meeting of the 32 nd National Chemistry Congress held on September 17-19 by Turkish Chemical Society, Turkey.
Tarihler

Başvuru Tarihi : 2 Kasım 2020
Kabul Tarihi : 12 Ocak 2021
Yayımlanma Tarihi : 28 Şubat 2021

Vancouver Ardic Alidagi H , Çetindere S . A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties. Journal of the Turkish Chemical Society Section A: Chemistry. 2021; 8(1): 311-320.