Photophysical properties of 1-pyridine-3-phenylpyrazoloquinoline and molecular logic gate implementation

Tomasz Uchacz , Paweł Szlachcic , Andrzej Danel , Mercedes Kukułka , Monika Srebro-Hooper , Grzegorz Stopa , Katarzyna M. Stadnicka

Abstract

The work demonstrates the photophysical properties of 1-(2-pyridyl)-3-phenyl-pyrazolo[3,4-b]quinoline with the focus on the effect of pyridyl substituent on excited-state deactivation of the pyrazoloquinoline core, and on the molecular logic gate implementation. The deactivation mechanism of the singlet excited state was investigated by means of UV-vis absorption, steady-state and time-resolved fluorescence spectroscopy as well as nanosecond laser flash photolysis. The maximum of absorption (emission) in nonpolar cyclohexane is located at 385 nm (421 nm) and only slightly depends on solvent polarity. The compound exhibits a moderate fluorescence (up to 42%) and a low-temperature phosphorescence (77 K). The studies reveal that the pyridyl group modifies the deactivation mechanism by triggering efficient intersystem crossing. Moreover, the effect of various chemical species: proton, electron-donating amine, and dihydrogenphosphate anion on the absorption and emission of the investigated dye was evaluated. The interpretation of the fluorescence behaviour in the presence or absence of the chemical inputs leads to the realization of unimolecular logic circuits that are able to perform advanced arithmetic operations, such as subtraction (XOR/INH) or IMP/INH logic circuit. The experimental results were supported by quantum-chemical calculations.
Author Tomasz Uchacz
Tomasz Uchacz,,
-
, Paweł Szlachcic (FoFT / IoCh)
Paweł Szlachcic,,
- Institute of chemistry
, Andrzej Danel (FoFT / IoCh)
Andrzej Danel,,
- Institute of chemistry
, Mercedes Kukułka
Mercedes Kukułka,,
-
, Monika Srebro-Hooper
Monika Srebro-Hooper,,
-
, Grzegorz Stopa
Grzegorz Stopa,,
-
, Katarzyna M. Stadnicka
Katarzyna M. Stadnicka,,
-
Journal seriesDyes and Pigments, ISSN 0143-7208, e-ISSN 1873-3743, (N/A 100 pkt)
Issue year2019
Vol166
Pages490-501
Publication size in sheets0.55
Keywords in EnglishPyridine-substituted pyrazoloquinoline, Intramolecular charge transfer emission, Molecular logic device half-subtractor, Intersystem crossing process, Photoinduced electron transfer quenching
ASJC Classification1500 General Chemical Engineering; 1508 Process Chemistry and Technology
DOIDOI:10.1016/j.dyepig.2019.03.031
URL https://www.sciencedirect.com/science/article/pii/S0143720819301159/pdfft?md5=69063380bce0e5cb284796dd4b87588c&pid=1-s2.0-S0143720819301159-main.pdf
Internal identifierWTŻ/2019/29
Languageen angielski
Score (nominal)100
Score sourcejournalList
Publication indicators WoS Citations = 2; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 0.909; WoS Impact Factor: 2018 = 4.018 (2) - 2018=3.582 (5)
Citation count*3 (2020-06-05)
Additional fields
FinansowanieThe research was carried out with the equipment purchased thanks to the financial support of the European Regional Development Fund in the framework of the Polish Innovation Economy Operational Program (contract no. POIG.02.01.00-12-023/08).
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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