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Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials

Paper ID Volume ID Publish Year Pages File Format Full-Text
27271 44013 2012 9 PDF Available
Title
Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials
Abstract

The synthesized benzothiadiazole-based series fluorophores as potential wavelength-shifting materials exhibit large Stokes shifts (>160 nm) with multiple broad absorbance bands from UV region to 600 nm and a strong fluorescence peak around 700 nm (in CHCl3). Intramolecular charge transfer (ICT) characters of the synthesized compounds are examined using UV–vis and photoluminescence solvatochromic shift measurements. Among the synthesized compounds, the fluorophores with asymmetrical structures exhibit larger Stokes shifts than those with symmetrical structures due to large dipole moment changes upon excitation. The fluorophores with electron-donating methoxyl groups attached to the triphenylamine donors are found to have strong ICT properties. Photophysical experimental results are supported by theoretical calculations using Density Function Theory (DFT) and Time Dependent Density Function Theory (TD-DFT) methods. Calculated frontier molecular orbitals (MOs) of ground states on these fluorophores showed an increase in ICT character up to 50% from HOMO to LUMO. Geometric optimization calculations of the excited state reveal that these fluorophores show a more planar structure for the excited state than the ground state, which allows more π–π* overlap and leads to larger Stokes shifts and higher quantum yields.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► The benzothiadiazole-based fluorophores were synthesized as wavelength-shifting materials for improving the efficiency of man-made solar cells. ► They show specific spectral properties with absorbance from UV to 600 nm and strong emission around 700 nm. ► Their large Stokes shifts were due to the strong intramolecular charge transfer effect during excitation. ► More planar geometry in their excitation states gave them higher quantum yields.

Keywords
Benzothiadiazole; Wavelength-shifting materials; Large Stokes shift; ICT; DFT
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Synthesis and characterizations of benzothiadiazole-based fluorophores as potential wavelength-shifting materials
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 231, Issue 1, 1 March 2012, Pages 51–59
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us