Keywords

Squaraine dye, pyrene, photophysical property, pi conjugation

Abstract

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 × 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.

Notes

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Graduation Date

2015

Semester

Spring

Advisor

Belfield, Kevin

Degree

Master of Science (M.S.)

College

College of Sciences

Department

Chemistry

Degree Program

Chemistry

Format

application/pdf

Identifier

CFE0006024

URL

http://purl.fcla.edu/fcla/etd/CFE0006024

Language

English

Release Date

November 2016

Length of Campus-only Access

1 year

Access Status

Masters Thesis (Open Access)

Subjects

Dissertations, Academic -- Sciences; Sciences -- Dissertations, Academic

Restricted to the UCF community until November 2016; it will then be open access.

Included in

Chemistry Commons

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