Effect of the electron donating group on the excited-state electronic nature and epsilon-near-zero properties of curcuminoid-borondifluoride dyes

Kyu Ri Choi, Dae Hyeon Kim, Yeon Ui Lee, Virginie Placide, Steven Huynh, Dandan Yao, Gabriel Canard, Elena Zaborova, Fabrice Mathevet, Loïc Mager, Benoît Heinrich, Jean Charles Ribierre, Jeong Weon Wu, Frédéric Fages, Anthony D'Aléo

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1 Scopus citations

Abstract

Epsilon-near-zero (ENZ) properties have been reported in organic molecular films. In particular, cyanine and squaraine films have been shown to exhibit ENZ properties in the visible spectral region with a strong 3rd order nonlinear optical response near the ENZ spectral region. Noting both cyanine and squaraine belong to the polymethine family, a series of six curcuminoid borondifluoride (Curc) derivatives were developed to examine whether such a polymethine character is positively correlated with the ENZ property of the organic films. Those Curc derivatives possess a Donor-Acceptor-Donor (D-A-D) architecture with acceptor, AcacBF2, located at the molecular center. The backbone of Curc is designed such that the donor strength can be tuned to transit between charge transfer (CT) and polymethine character. This balance between CT and polymethine character of the Curc series is examined based on the Lippert-Mataga plot. As donor strength in the D-A-D structure increases, CT character is less marked resulting in a more dominant polymethine character. The structural and optical properties of the Curc films with a thickness in the order of 30 nm were examined to correlate the polymethine character with the ENZ response. The results obtained in isotropic Curc thin films demonstrate that an increase of polymethine character associated with a stronger donor strength leads to an appearance/enhancement of the ENZ property in the visible spectrum range from 500 to 670 nm. Overall, this study provides useful guidelines to engineer new organic materials showing ENZ properties in a desired spectral range.

Original languageEnglish
Pages (from-to)38247-38257
Number of pages11
JournalRSC Advances
Volume11
Issue number60
DOIs
StatePublished - 29 Nov 2021

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