2,15-Dibutoxy-6,11-dicyano[6]Helicene (CN-HEL) has been prepared through a two-step sequence under mild conditions, in an overall 78% yield, starting from 2,7-bis(cyanomethyl)naphthalene as a suitable material. The Helicene has been experimentally characterized and its absorption and photoluminescence (PL) properties have been evaluated showing a blue emission in the visible spectrum. A strong absorption is entirely in the UV region (lambda(max) = 290 nm), yet fluorescence occurs at 400 nm. This equates to a Stokes shift of 1.17 eV (9482 cm(-1)) which is among the largest Stokes shifts reported for small molecules, making it a promising candidate for optoelectronic applications. Furthermore, the( 1)H NMR, FT-IR, UV-vis and PL spectra were computed by means of the very efficient time-dependent density functional theory (TD-DFT) approach. The computed spectra with two recommended density functional (PBEPBE and cam/B3LYP) and extended basis sets compare very well with the corresponding experimental data. HOMO and LUMO energy levels were also investigated experimentally, showing an electrochemical band gap of 2.54 eV. Results obtained throughout this work are of great importance and prove the relevance of the target Helicene to be used in a wide range of both existing and new applications such as fluorescence probes and molecular sensors.

(2022). 2,15-dibutoxy-6,11-dicyano[6]Helicene: Synthesis, electrochemical, photophysical properties and computational studies [journal article - articolo]. In JOURNAL OF MOLECULAR STRUCTURE. Retrieved from http://hdl.handle.net/10446/228920

2,15-dibutoxy-6,11-dicyano[6]Helicene: Synthesis, electrochemical, photophysical properties and computational studies

Fontana, Francesca;
2022

Abstract

2,15-Dibutoxy-6,11-dicyano[6]Helicene (CN-HEL) has been prepared through a two-step sequence under mild conditions, in an overall 78% yield, starting from 2,7-bis(cyanomethyl)naphthalene as a suitable material. The Helicene has been experimentally characterized and its absorption and photoluminescence (PL) properties have been evaluated showing a blue emission in the visible spectrum. A strong absorption is entirely in the UV region (lambda(max) = 290 nm), yet fluorescence occurs at 400 nm. This equates to a Stokes shift of 1.17 eV (9482 cm(-1)) which is among the largest Stokes shifts reported for small molecules, making it a promising candidate for optoelectronic applications. Furthermore, the( 1)H NMR, FT-IR, UV-vis and PL spectra were computed by means of the very efficient time-dependent density functional theory (TD-DFT) approach. The computed spectra with two recommended density functional (PBEPBE and cam/B3LYP) and extended basis sets compare very well with the corresponding experimental data. HOMO and LUMO energy levels were also investigated experimentally, showing an electrochemical band gap of 2.54 eV. Results obtained throughout this work are of great importance and prove the relevance of the target Helicene to be used in a wide range of both existing and new applications such as fluorescence probes and molecular sensors.
articolo
Raouafi, Sondes; Chemek, Mourad; Fontana, Francesca; Alimi, Kamel; Aloui, Faouzi
(2022). 2,15-dibutoxy-6,11-dicyano[6]Helicene: Synthesis, electrochemical, photophysical properties and computational studies [journal article - articolo]. In JOURNAL OF MOLECULAR STRUCTURE. Retrieved from http://hdl.handle.net/10446/228920
File allegato/i alla scheda:
File Dimensione del file Formato  
Draft manuscript Aloui.pdf

embargo fino al 21/07/2024

Descrizione: This in an Accepted Manuscript of an article published on Journal of Molecular Structure (2022), doi: https://doi.org/10.1016/j.molstruc.2022.133680
Versione: postprint - versione referata/accettata senza referaggio
Licenza: Creative commons
Dimensione del file 1.81 MB
Formato Adobe PDF
1.81 MB Adobe PDF   Visualizza/Apri
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

Aisberg ©2008 Servizi bibliotecari, Università degli studi di Bergamo | Terms of use/Condizioni di utilizzo

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10446/228920
Citazioni
  • Scopus 0
  • ???jsp.display-item.citation.isi??? 0
social impact