Skip to main content

Advertisement

SpringerLink
Log in

Synthesis of Novel Carbazole Fused Coumarin Derivatives and DFT Approach to Study Their Photophysical Properties

  • ORIGINAL PAPER
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Novel coumarin derivatives have been synthesized by the classical Knoevenagel condensation of 4-hydroxy-9-methyl-9H-carbazole-3-carbaldehyde with active methylene compounds and characterized. Effect of solvent polarity on the photophysical properties, absorption and emission has been studied. The photophysical properties of the synthesized coumarins have been compared with some of the established analogous coumarin derivatives. Investigation of the structural parameters and understanding photophysical properties of the synthesized coumarin derivatives were carried out using Density Functional Theory (DFT) and Time Dependant Density Functional Theory (TDDFT) computations. The experimental values were correlated with the theoretical derived results. The ratio of the excited state and the ground state dipole moments was calculated by using solvatochromic and solvatofluoric data and compared with the values obtained from DFT and TDDFT computations.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Li H, Cai L, Chen Z (2012) Coumarin-derived fluorescent chemosensors. In: Wang W (ed) Adv Chem Sensors pp 121–150

  2. Drexhage KH (1973) Dye lasers. Topics in applied physics

  3. Krasovitskii BM (1988) Organic luminescent materials. Wiley-VCH Weinheim, Germany

    Google Scholar 

  4. Nourmohammadian F, Gholami MD (2010) Microwave-promoted one-pot syntheses of coumarin dyes. Synth Commun 40:901–909

    Article  CAS  Google Scholar 

  5. Essaïdi Z, Krupka O, Iliopoulos K et al (2013) Synthesis and functionalization of coumarin-containing copolymers for second order optical nonlinearities. Opt Mater (Amst) 35:576–581

    Article  Google Scholar 

  6. Maity D, Karthigeyan D, Kundu TK, Govindaraju T (2013) FRET-based rational strategy for ratiometric detection of Cu2+ and live cell imaging. Sensors Actuators B Chem 176:831–837

    Article  CAS  Google Scholar 

  7. Ye D, Wang L, Li H et al (2013) Synthesis of coumarin-containing conjugated polymer for naked-eye detection of DNA and cellular imaging. Sensors Actuators B Chem 181:234–243

    Article  CAS  Google Scholar 

  8. Signore G, Nifosì R, Albertazzi L et al (2010) Polarity-sensitive coumarins tailored to live cell imaging. J Am Chem Soc 132:1276–1288

    Article  CAS  PubMed  Google Scholar 

  9. Wang T, Zhao Y, Shi M, Wu F (2007) The synthesis of novel coumarin dyes and the study of their photoreaction properties. Dye Pigment 75:104–110

    Article  CAS  Google Scholar 

  10. Corrie JET, Munasinghe VRN, Rettig W (2000) Synthesis and fluorescence properties of substituted 7-aminocoumarin-3-carboxylate derivatives. J Heterocycl Chem 37:1447–1455

    Article  CAS  Google Scholar 

  11. Lin Q, Bao C, Fan G et al (2012) 7-amino coumarin based fluorescent phototriggers coupled with nano/bio-conjugated bonds: synthesis, labeling and photorelease. J Mater Chem 22:6680–6688

    Article  CAS  Google Scholar 

  12. Grandberg II, Denisov LK, Popova OA (1987) 7-aminocoumarins (Review). Chem Heterocycl Compd 23:117–142

    Article  Google Scholar 

  13. Reddy AR, Prasad DV, Darbarwar M (1986) Absorption and fluorescence spectra of 7-aminocoumarin derivatives. J Photochem 32:69–80

    Article  CAS  Google Scholar 

  14. Kim E, Park SB (2010) In: Demchenko AP (ed) Advanced fluorescence reporters in chemistry and biology I: fundamentals and biology, fundamentals and molecular design. Springer, Heidelberg, pp 150–155

    Google Scholar 

  15. Jagtap AR, Satam VS, Rajule RN, Kanetkar VR (2009) The synthesis and characterization of novel coumarin dyes derived from 1,4-diethyl-1,2,3,4-tetrahydro-7-hydroxyquinoxalin-6-carboxaldehyde. Dye Pigment 82:84–89

    Article  CAS  Google Scholar 

  16. Besson T, Coudert G, Guillaumet G (1991) Synthesis and fluorescent properties of some heterobifunctional and rigidized 7-aminocoumarins. J Heterocycl Chem 28:1517–1523

    Article  CAS  Google Scholar 

  17. Reynolds GA, Drexhage KH (1975) New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers. Opt Commun 13:222–225

    Article  CAS  Google Scholar 

  18. Abdel-Mottaleb MSA, Antonious MS, Abo-Aly MM et al (1989) Photophysics and dynamics of rigidized coumarin laser dyes. J Photochem Photobiol A Chem 50:259–273

    Article  CAS  Google Scholar 

  19. Wada T, Zhang Y, Choi YS, Sasabe H (1993) Photoconductive crystals for nonlinear optics: molecular design and crystal structure. J Phys D Appl Phys 26:B221

    Article  CAS  Google Scholar 

  20. Wada T, Zhang Y, Yamakado M, Sasabe H (1993) Linear and nonlinear optical properties of carbazole-containing polymers. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst 227:85–92

    Article  CAS  Google Scholar 

  21. Chang C-C, Kuo I-C, Lin J-J et al (2004) A novel carbazole derivative, BMVC: a potential antitumor agent and fluorescence marker of cancer cells. Chem Biodivers 1:1377–1384

    Article  CAS  PubMed  Google Scholar 

  22. Qian Y, Xiao G, Wang G et al (2006) Synthesis and third-order optical nonlinearity in two-dimensional A-π-D-π-A carbazole-cored chromophores. Dye Pigment 71:109–117

    Article  CAS  Google Scholar 

  23. Fitilis I, Fakis M, Polyzos I et al (2007) A two-photon absorption study of fluorene and carbazole derivatives. The role of the central core and the solvent polarity. Chem Phys Lett 447:300–304

    Article  CAS  Google Scholar 

  24. Li H, Zhang Y, Hu Y et al (2004) Novel soluble N-phenyl-carbazole-containing PPVs for light-emitting devices: synthesis, electrochemical, optical, and electroluminescent properties. Macromol Chem Phys 205:247–255

    Article  CAS  Google Scholar 

  25. Thomas KRJ, Lin JT, Tao Y-T, Ko C-W (2000) Novel green light-emitting carbazole derivatives: potential electroluminescent materials. Adv Mater 12:1949–1951

    Article  CAS  Google Scholar 

  26. Kuo W-J, Hsiue G-H, Jeng R-J (2002) Synthesis and macroscopic second-order nonlinear optical properties of poly(ether imide)s containing a novel two-dimensional carbazole chromophore with nitro acceptors. J Mater Chem 12:868–878

    Article  CAS  Google Scholar 

  27. Zhou Y, Wang F, Kim Y et al (2009) Cu2+−selective ratiometric and “off-on” sensor based on the rhodamine derivative bearing pyrene group. Org Lett 11:4442–4445

    Article  CAS  PubMed  Google Scholar 

  28. Ravi M, Samanta A, Radhakrishnan TP (1994) Excited state dipole moments from an efficient analysis of solvatochromic stokes shift data. J Phys Chem 98:9133–9136

    Article  Google Scholar 

  29. Lippert E (1957) Spektroskopische bestimmung des dipolmomentes aromatischer verbindungen im ersten angeregten singulettzustand. Zeitschrift für Elektrochem Ber Bunsenges Phys Chem 61:962–975

    CAS  Google Scholar 

  30. Mataga N, Kaifu Y, Koizumi M (1955) The solvent effect on fluorescence spectrum, change of solute-solvent interaction during the lifetime of excited solute molecule. Bull Chem Soc Jpn 28:690–691

    Article  CAS  Google Scholar 

  31. Mataga N (1963) Solvent effects on the absorption and fluorescence spectra of naphthylamines and isomeric aminobenzoic acids. Bull Chem Soc Jpn 36:654–662

    Article  CAS  Google Scholar 

  32. Mataga N, Kaifu Y, Koizumi M (1956) Solvent effects upon fluorescence spectra and the dipolemoments of excited molecules. Bull Chem Soc Jpn 29:465–470

    Article  CAS  Google Scholar 

  33. Reichardt C (2002) Solvents and solvent effects in organic chemistry

  34. Ravi M, Soujanya T, Samanta A, Radhakrishnan TP (1995) Excited-state dipole moments of some coumarin dyes from a solvatochromic method using the solvent polarity parameter, E N T. J Chem Soc Faraday Trans 91:2739

    Article  Google Scholar 

  35. Kumar S, Rao VC, Rastogi RC (2001) Excited-state dipole moments of some hydroxycoumarin dyes using an efficient solvatochromic method based on the solvent polarity parameter, ETN. Spectrochim Acta Part A Mol Biomol Spectrosc 57:41–47

    Article  CAS  Google Scholar 

  36. Masternak A, Wenska G, Milecki J et al (2005) Solvatochromism of a novel Betaine dye derived from purine. J Phys Chem A 109:759–766

    Article  CAS  PubMed  Google Scholar 

  37. Nemkovich NA, Pivovarnko VG, Baumann W et al (2005) Dipole moments of 4 -aminoflavonol fluorescent probes in different solvents. J Fluoresc 15:29–36

    Article  CAS  PubMed  Google Scholar 

  38. Aaron J-J, Maafi M, Kersebet C et al (1996) A solvatochromic study of new benzo[a]phenothiazines for the determination of dipole moments and specific solute—solvent interactions in the first excited singlet state. J Photochem Photobiol A Chem 101:127–136

    Article  CAS  Google Scholar 

  39. Raikar US, Renuka CG, Nadaf YF et al (2006) Rotational diffusion and solvatochromic correlation of coumarin 6 laser dye. J Fluoresc 16:847–854

    Article  CAS  PubMed  Google Scholar 

  40. Inamdar SR, Nadaf YF, Mulimani BG (2003) Ground and excited state dipole moments of exalite 404 and exalite 417 UV laser dyes determined from solvatochromic shifts of absorption and fluorescence spectra. J Mol Struct THEOCHEM 624:47–51

    Article  CAS  Google Scholar 

  41. Harbison GS (2002) The electric dipole polarity of the ground and low-lying metastable excited states of NF. J Am Chem Soc 124:366–367

    Article  CAS  PubMed  Google Scholar 

  42. Hodge CN, Aldrich PE, Wasserman ZR et al (1999) Corticotropin-releasing hormone receptor antagonists: framework design and synthesis guided by ligand conformational studies. J Med Chem 42:819–832

    Article  CAS  PubMed  Google Scholar 

  43. Józefowicz M, Heldt JR (2007) Dipole moments studies of fluorenone and 4-hydroxyfluorenone. Spectrochim Acta Part A Mol Biomol Spectrosc 67:316–320

    Article  Google Scholar 

  44. Bakhshiev NG (1964) Opt Spektrosk 16:821–832

    CAS  Google Scholar 

  45. Kawski A (1966) Zur lösungsmittelabhängigkeit der wellenzahl von elektronenbanden lumineszierender moleküle und über die bestimmung der elektrischen dipolmomente im anregungszustand. Acta Phys Polon 29:507–518

    CAS  Google Scholar 

  46. Chamma A, Viallet PCR (1970) Determination du moment dipolaire d’une molecule dans un etat excite singulet. Acad Sci Paris Ser C 270:1901–1904

    CAS  Google Scholar 

  47. Kawski A (1964) Dipolmomente einiger Naphthole im Grund- und Anregungszustand. Naturwissenschaften 51:82–83

    Article  CAS  Google Scholar 

  48. Treutler O, Ahlrichs R (1995) Efficient molecular numerical integration schemes. J Chem Phys 102:346–354

    Article  CAS  Google Scholar 

  49. Cossi M, Barone V, Cammi R, Tomasi J (1996) Ab initio study of solvated molecules: a new implementation of the polarizable continuum model. Chem Phys Lett 255:327–335

    Article  CAS  Google Scholar 

  50. Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3094

    Article  CAS  PubMed  Google Scholar 

  51. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789

    Article  CAS  Google Scholar 

  52. Kim CH, Park J, Seo J et al (2010) Excited state intramolecular proton transfer and charge transfer dynamics of a 2-(2′-hydroxyphenyl)benzoxazole derivative in solution. J Phys Chem A 114:5618–5629

    Article  CAS  PubMed  Google Scholar 

  53. Casida ME, Jamorski C, Casida 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 108:4439–4449

    Article  CAS  Google Scholar 

  54. Furche F, Rappaport D (2005) Density functional theory for excited states: equilibrium structure and electronic spectra. In: Computational photochemistry

  55. Hehre WJ, Radom L, Schleyer PV, Pople J (1986) Ab initio molecular orbital theory. Wiley, New York

    Google Scholar 

  56. Bauernschmitt R, Ahlrichs R (1996) Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem Phys Lett 256:454–464

    Article  CAS  Google Scholar 

  57. Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. New York, Kluwer Academic

    Book  Google Scholar 

  58. Phatangare KR, Gupta VD, Tathe AB et al (2013) ESIPT inspired fluorescent 2-(4-benzo[d]oxazol-2-yl)naphtho[1,2-d]oxazol-2-yl)phenol: experimental and DFT based approach to photophysical properties. Tetrahedron 69:1767–1777

    Article  CAS  Google Scholar 

  59. Valeur B, Berberan-Santos MN (2001) Molecular fluorescence: principles and applications. Weinheim, Wiley-VCH Verlag

    Book  Google Scholar 

  60. Frisch MJ, Trucks GW, Schlegel HB et al (2009) Gaussian 09, Revision C.01. Gaussian 09, Revis B.01. Gaussian, Inc, Wallingford

    Google Scholar 

Download references

Acknowledgments

Prashant G. Umape is thankful to UGC-CAS for providing research fellowship under Special Assistance Programme (SAP). Sandip K. Lanke is thankful to UGG-CSIR for senior research fellowship.

Author information

Authors and Affiliations

  1. Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, (Formerly UDCT), Nathalal Parekh Marg, Matunga, Mumbai, 400 019, India

    Nagaiyan Sekar, Prashant G. Umape & Sandip K. Lanke

Authors
  1. Nagaiyan Sekar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Prashant G. Umape
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sandip K. Lanke
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nagaiyan Sekar.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(DOCX 111 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sekar, N., Umape, P.G. & Lanke, S.K. Synthesis of Novel Carbazole Fused Coumarin Derivatives and DFT Approach to Study Their Photophysical Properties. J Fluoresc 24, 1503–1518 (2014). https://doi.org/10.1007/s10895-014-1436-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-014-1436-6

Keywords

Search

Navigation