Skip to main content
SpringerLink
Log in

Structural and morphological studies of meso-ethylcarbazole F-BODIPY thin films

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

In this work, we describe the synthesis of meso-(9-ethyl-9H-carbazol-3-yl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene and its incorporation as thin film by vapor deposition on indium tin oxide. The morphology of the film was analyzed by scanning electron microscopy and atomic force microscopy showing a granular and homogeneous structure, contact angle measurements revealed that this film exhibits a hydrophobic surface. Packing of the compound was simulated through molecular dynamics and Monte Carlo sampling, and the electronic features of aggregates were modeled with plane-wave DFT. A semiconductor behavior for the featured compound in aggregated state, which compares well with systems applied on electronic devices, is predicted for the featured F-BODIPY.

Graphical Abstract

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Lu H, Mack J, Yanga Y, Shen Z (2014) Chem Soc Rev 43:4778

    Article  CAS  Google Scholar 

  2. Heugebaert TSA, Roman BI, Stevens CV (2012) Chem Soc Rev 41:5626

    Article  CAS  Google Scholar 

  3. Gryko DT, Gryko D, Lee CH (2012) Chem Soc Rev 41:3780

    Article  CAS  Google Scholar 

  4. Loudret A, Burgess K (2007) Chem Rev 107:4891

    Article  Google Scholar 

  5. Ulrich G, Ziessel R, Harriman A (2008) Angew Chem Int Ed 47:1184

    Article  CAS  Google Scholar 

  6. Zhu S, Dorh N, Zhang J, Vegesna G, Li H, Luo FT, Tiwari A, Liu H (2012) J Mater Chem 22:2781

    Article  CAS  Google Scholar 

  7. Sobenina LN, Petrova OV, Petrushenko KB, Ushakov IA, Mikhaleva AI, Meallet-Renault R, Trofimov BA (2013) Eur J Org Chem 19:4107

    Article  Google Scholar 

  8. Collado D, Vida Y, Najera F, Perez-Inestrosa E (2014) RSC Adv 4:2306

    Article  CAS  Google Scholar 

  9. Bonardi L, Kanaan H, Camerel F, Jolinat P, Retailleau P, Ziessel R (2008) Adv Funct Mater 18:401

    Article  CAS  Google Scholar 

  10. Kumbhar HS, Gadilohar BL, Shankarling GS (2015) Spectrochim Acta Part A Mol Biomol Spectrosc 146:80

    Article  CAS  Google Scholar 

  11. Ueno T, Urano Y, Kojima H, Nagano T (2006) J Am Chem Soc 128:10640

    Article  CAS  Google Scholar 

  12. Mei Y, Bentley PA, Wang W (2006) Tetrahedron Lett 47:2447

    Article  CAS  Google Scholar 

  13. Guo S, Ma L, Zhao J, Küçüköz B, Karatay A, Hayvali M, Yaglioglu HG, Elmali A (2014) Chem Sci 5:489

    Article  CAS  Google Scholar 

  14. French AN, Wilson SR, Welch MJ, Katzenellenbogen JA (1993) Steroids 58:157

    Article  CAS  Google Scholar 

  15. Kamkaew A, Lim SH, Lee HB, Kiew LV, Chung LY, Burgess K (2013) Chem Soc Rev 42:77

    Article  CAS  Google Scholar 

  16. Poe A, Della Pelle A, Subrahmanyam A, White W, Wantz G, Thayumariavan S (2014) Chem Commun 50:2913

    Article  CAS  Google Scholar 

  17. Mao M, Zhang X, Cao L, Tong Y, Wu G (2015) Dyes Pigm 117:28

    Article  CAS  Google Scholar 

  18. Liu CL, Chen Y, Shelar DP, Li C, Chen G, Fu WF (2014) J Mat Chem C 2:5471

    Article  CAS  Google Scholar 

  19. Kesavan PE, Gupta I (2014) Dalton Trans 43:12405

    Article  CAS  Google Scholar 

  20. Kesavan PE, Das S, Lone MY, Jha PC, Mori S, Gupta I (2015) Dalton Trans 44:17209

    Article  CAS  Google Scholar 

  21. Thorat KG, Kamble P, Ray AK, Sekar N (2015) Phys Chem Chem Phys 17:17221

    Article  CAS  Google Scholar 

  22. Sengul IF, Okutan E, Kandemir H, Astarci E, Cosut B (2015) Dyes Pigm 123:32

    Article  CAS  Google Scholar 

  23. Khan TK, Jana SK, Rao MR, Shaik MS, Ravikanth M (2012) Inorg Chim Acta 383:257

    Article  CAS  Google Scholar 

  24. Qin W, Baruah M, Auweraer MVD, De Schryver FC, Boens N (2005) J Phys Chem A 109:7371

    Article  CAS  Google Scholar 

  25. Lakshmi V, Ravikanth M (2012) Dalton Trans 41:5903

    Article  CAS  Google Scholar 

  26. Xochitiotzi-Flores E, Islas-Mejía AA, García-Ortega H, Romero-Ávila M, Méndez-Stivalet JM, Carreón-Castro MD, Santillan R, Maldonado-Dominguez M, Arcos-Ramos R, Farfán N (2016) J Organomet Chem 805:148

    Article  CAS  Google Scholar 

  27. Moon H, Zeis R, Borkent EJ, Besnard C, Lovinger AJ, Siegrist T, Kloc C, Bao ZN (2004) J Am Chem Soc 126:15322

    Article  CAS  Google Scholar 

  28. Materials Studio 8.0.0.843, Dassault Systèmes, 2014

  29. Zhao Y, Truhlar DG (2006) J Chem Phys 125:194101

    Article  Google Scholar 

  30. Hotta S, Yamao T, Zulkarnaen-Bisri S, Takenobu T, Iwasa Y (2014) J Mater Chem C 2:965

    Article  CAS  Google Scholar 

  31. Bawendi MG, Freed KF, Mohanty U (1986) J Chem Phys 84:7036

    Article  CAS  Google Scholar 

  32. Eichinger BE, Rigby D, Muir MH (1995) Comput Polym Sci 5:147

    CAS  Google Scholar 

  33. Clark SJ, Segall MD, Pickard CJ, Hasnip PJ, Probert MJ, Refson K, Payne MC (2005) Z Kristallogr 220:567

    CAS  Google Scholar 

  34. Ando S, Murakami R, Nishida J, Tada H, Inoue J, Tokito S, Yamashita Y (2005) J Am Chem Soc 127:14996

    Article  CAS  Google Scholar 

  35. Nosè S (1984) J Chem Phys 81:511

    Article  Google Scholar 

  36. Berendsen HJC, Postma JPM, van Gunsteren WF, DiNola A, Haak JR (1984) J Chem Phys 81:3684

    Article  CAS  Google Scholar 

  37. Rappe AK, Casewit CJ, Colwell KS, Goddard WA III, Skiff WM (1992) J Am Chem Soc 114:10024

    Article  CAS  Google Scholar 

  38. Newman M (2003) J Appl Cryst 36:356

    Article  Google Scholar 

  39. Visser JW (1969) J Appl Cryst 2:89

    Article  CAS  Google Scholar 

Download references

Acknowledgments

MDP Carreón-Castro, M. Rivera-Hernández, and N. Farfán acknowledge DGAPA-PAPIIT IN-116716, IN-106513 and IN-216616 projects, respectively. O. Amelines-Sarria acknowledges financial support from DGAPA CJIC/CTIC/1334/2013. R. Arcos-Ramos and R. Corona-Sánchez thank to DGAPA-UNAM for granted postdoctoral fellowships. Thanks are due to E. Palacios-Boneta and C.R. Magaña for technical and SEM assistance.

Author information

Authors and Affiliations

  1. Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, 04510, Ciudad de México, Mexico

    Ricardo Corona-Sánchez, Mauricio Maldonado-Domínguez, Alberto Jerezano-Domínguez, Héctor García-Ortega & Norberto Farfán

  2. Departamento de Química de Radiaciones y Radioquímica, Instituto de Ciencias Nucleares, Universidad Nacional Autónoma de México, 04510, Ciudad de México, Mexico

    Rafael Arcos-Ramos & María del Pilar Carreón-Castro

  3. Departamento de Materia Condensada, Instituto de Física, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Ciudad de México, Mexico

    Margarita Rivera

  4. Centro de Investigación y Desarrollo Tecnológico en Energías Renovables, Universidad de Ciencias y Artes de Chiapas, Libramiento Norte Poniente No. 1150, Col. Lajas Maciel, Tuxtla Gutiérrez, Chiapas, Mexico

    Oscar Amelines-Sarria

Authors
  1. Ricardo Corona-Sánchez
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rafael Arcos-Ramos
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mauricio Maldonado-Domínguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Oscar Amelines-Sarria
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alberto Jerezano-Domínguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Héctor García-Ortega
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Margarita Rivera
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. María del Pilar Carreón-Castro
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Norberto Farfán
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Norberto Farfán.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 7695 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Corona-Sánchez, R., Arcos-Ramos, R., Maldonado-Domínguez, M. et al. Structural and morphological studies of meso-ethylcarbazole F-BODIPY thin films. Monatsh Chem 147, 1915–1923 (2016). https://doi.org/10.1007/s00706-016-1760-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1760-4

Keywords

Search

Navigation