STUDY OF BODIPY DERIVATIVE COMPOUNDS AS PH INDICATORS AND THEIR APPLICATION IN CHEMISTRY EXPERIMENT MODULE
Acidity or pH plays a crucial role in life, such as affecting the taste of fruits and the function of household products. Common pH indicators have limitations, including less accurate readings, susceptibility to contamination by other substances, and difficulty in measuring low-concentration...
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| Format: | Theses |
| Language: | Indonesia |
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| Online Access: | https://digilib.itb.ac.id/gdl/view/87533 |
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| Institution: | Institut Teknologi Bandung |
| Language: | Indonesia |
| Summary: | Acidity or pH plays a crucial role in life, such as affecting the taste of fruits and the
function of household products. Common pH indicators have limitations, including
less accurate readings, susceptibility to contamination by other substances, and
difficulty in measuring low-concentration samples. Fluorescence-based pH
measurement techniques are advantageous because of their non-destructive nature,
high sensitivity and specificity, ease of use, and require only a small amount of
sample. BODIPY, also known as boron-dipyrromethene, is a fluorescent compound
that is thermally and photochemically stable, exhibits high fluorescence quantum
yields, and can be easily synthesized and modified. Therefore, this research aimed
to synthesize phenolic BODIPY compounds (3-allyl-4-hydroxyphenyl BODIPY 3c)
and phenyl BODIPY compounds with electron-donating substituents (4
fluorophenyl BODIPY 3a and 4-allyloxyphenyl BODIPY 3b), investigate the
properties of these BODIPY compounds (3a–3c), along with vanillin BODIPY (3d)
in relation to pH levels using UV-Vis and fluorescence spectroscopy techniques, and
develop a chemistry experiment module for acid-base fluorescence concept.
BODIPY 3a–3c were successfully synthesized with yields ranging from 21.7% to
91.4%. UV-Vis spectroscopy showed that BODIPY compounds 3a and 3b were
stable at pH 1–11.9, whereas BODIPY compounds 3c and 3d formed hemi-quinone
species at pH 10–11.9. Fluorescence spectroscopy revealed a slight decrease in the
fluorescence intensity of BODIPY compounds 3a and 3b under both acidic and
basic conditions. In contrast, BODIPY compounds 3c and 3d showed increased
intensity under acidic conditions but decreased intensity under basic conditions.
The fluorescence quantum yields of BODIPY compounds 3a–3d in CH2Cl2 were in
the range of 0.06–0.15 and CH3CN 0.002–0.05 with rhodamine B as a reference.
These results indicated that phenolic BODIPY compounds have potential as
fluorescence-based pH indicators. Additionally, the chemical experiment module
was successfully developed as a supplementary resource for teaching the
fluorescence acid-base concept at the high school level. |
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