Non-peripherally alkylamino-substituted phthalocyanines: Synthesis, spectral, photophysical and acid-base properties

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F19%3A10399465" target="_blank" >RIV/00216208:11160/19:10399465 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=0QMOepqyvx" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=0QMOepqyvx</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1142/S108842461950024X" target="_blank" >10.1142/S108842461950024X</a>

Result language
angličtina
Original language name
Non-peripherally alkylamino-substituted phthalocyanines: Synthesis, spectral, photophysical and acid-base properties
Original language description
Non-peripherally substituted metal-free and zinc phthalocyanines (Pcs) bearing four diethylamino groups and four Br atoms were prepared. Optimal conditions for synthesis of corresponding precursor (i.e. 3-bromo-6-(diethylamino)phthalonitrile) either by nucleophilic substitution or by Buchwald-Hartwig coupling were studied. Noteworthy, 3,6-bis(diethylamino)phthalonitrile was also formed, nevertheless only at low yield (typically below 1%) and all attempts for its cyclotetramerization failed. Q bands of prepared Pcs were strongly red shifted up to the near-IR region (769 and 800 nm in THF for zinc and metal-free Pc, respectively). Unusually large hypsochromic shifts of the Q bands, 130 and 80 mn for metal-free and zinc Pc, respectively, were observed upon treating these Pcs with trifluoroacetic acid, which was attributed to the protonation of non-peripheral amines. Treatment with sulfuric acid led to subsequent protonation on the azomethine nitrogens as well. Photophysical study revealed low fluorescence emission of both derivatives (Phi(F), < 0.03, in THF) and efficient singlet oxygen production only for zinc Pc (Phi(Delta) = 0.77 in THF and 0.60 in DMF).
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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