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Synthesis, linear and nonlinear photophysical characterization of two symmetrical pyrene-terminated squaraine derivatives in solution

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Date Issued:
2015
Abstract/Description:
Two indole-based squaraine dyes bonded to two pyrenyl groups through vinyl- and ethynyl- linkers were synthesized with the aim of enhancing the intramolecular charge transfer interaction in addition to improving their optical properties. The absorption and emission properties of these derivatives were determined in order to gain an insight into the intensity of this type of interaction, their aggregation behavior and compare them with results obtained through quantum chemical calculations. Both compounds presented high photochemical stability in THF, and the linear spectroscopic characterization revealed high extinction coefficients, large fluorescence quantum yields and relatively low tendency of forming excimers in several solvents. The nonlinear spectroscopic study revealed two-photon absorption cross section maxima greater than 10,000 GM (1 GM = 1 (&)#215; 10-50 cm4 s/photon), which are improved values in comparison with the indole-based squaraine core. The experimental results were compared with time-dependent DFT calculations. These observations propose a new trend in the formulation of highly absorbing organic molecules containing pyrenyl groups for the development of new materials with Organic Light-Emitting Diode (OLED) applications. Moreover, this work contributes to the study of intramolecular charge transfer interaction and its tailoring for the improvement of the linear and nonlinear optical properties.
Title: Synthesis, linear and nonlinear photophysical characterization of two symmetrical pyrene-terminated squaraine derivatives in solution.
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Name(s): Ballestas Barrientos, Alfonso, Author
Belfield, Kevin, Committee Chair
Harper, James, Committee Member
Clausen, Christian, Committee Member
University of Central Florida, Degree Grantor
Type of Resource: text
Date Issued: 2015
Publisher: University of Central Florida
Language(s): English
Abstract/Description: Two indole-based squaraine dyes bonded to two pyrenyl groups through vinyl- and ethynyl- linkers were synthesized with the aim of enhancing the intramolecular charge transfer interaction in addition to improving their optical properties. The absorption and emission properties of these derivatives were determined in order to gain an insight into the intensity of this type of interaction, their aggregation behavior and compare them with results obtained through quantum chemical calculations. Both compounds presented high photochemical stability in THF, and the linear spectroscopic characterization revealed high extinction coefficients, large fluorescence quantum yields and relatively low tendency of forming excimers in several solvents. The nonlinear spectroscopic study revealed two-photon absorption cross section maxima greater than 10,000 GM (1 GM = 1 (&)#215; 10-50 cm4 s/photon), which are improved values in comparison with the indole-based squaraine core. The experimental results were compared with time-dependent DFT calculations. These observations propose a new trend in the formulation of highly absorbing organic molecules containing pyrenyl groups for the development of new materials with Organic Light-Emitting Diode (OLED) applications. Moreover, this work contributes to the study of intramolecular charge transfer interaction and its tailoring for the improvement of the linear and nonlinear optical properties.
Identifier: CFE0006024 (IID), ucf:50999 (fedora)
Note(s): 2015-05-01
M.S.
Sciences, Chemistry
Masters
This record was generated from author submitted information.
Subject(s): Squaraine dye -- pyrene -- photophysical property -- pi-conjugation
Persistent Link to This Record: http://purl.flvc.org/ucf/fd/CFE0006024
Restrictions on Access: campus 2016-11-15
Host Institution: UCF

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