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Predominant effect of connecting atom and position of substituents on azomethine nitrogens' basicity in phthalocyanines

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F16%3A10335427" target="_blank" >RIV/00216208:11160/16:10335427 - isvavai.cz</a>

  • Result on the web

    <a href="http://www.worldscientific.com/doi/full/10.1142/S1088424616500747" target="_blank" >http://www.worldscientific.com/doi/full/10.1142/S1088424616500747</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1142/S1088424616500747" target="_blank" >10.1142/S1088424616500747</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Predominant effect of connecting atom and position of substituents on azomethine nitrogens' basicity in phthalocyanines

  • Original language description

    The basicity of azomethine nitrogens was studied on a series of phthalocyanines (Pcs) that differed in a position of substituent, i.e. peripherally (beta-series) and non-peripherally substituted Pcs (alpha-series), and in a type of substituent (alkylsulfanyl, alkyloxy or alkyl). Appropriate 3,6- or 4,5-disubstituted phthalonitriles were prepared either by nucleophilic substitution or by Negishi coupling. Target zinc Pcs were synthesized by Linstead method. The basicity was studied by the mean of absorption and H-1 NMR spectroscopies in chloroform upon titration with trifluoroacetic acid. Equilibrium constants (log K) indicated significant difference within the series. Basicity decreased as follows: alpha-alkyloxy >> alpha-alkylsulfanyl > beta-alkyloxy > beta-alkyl > beta-alkylsulfanyl similar to alpha-alkyl with log K higher than 7 down to 2.6 M-1. Increased basicity of alpha-alkyloxy and alpha-alkylsulfanyl Pcs is caused by the stabilization of trapped hydrogen at azomethine nitrogen via hydrogen bonding and van der Waals interactions, respectively. The basicity of beta-series clearly correlated with the electronic effects of substituents. H-1 NMR studies confirmed the possibility of the weak bonding interactions in alpha-alkyloxy and alpha-alkylsulfanyl Pcs, however, the position of the H-1 NMR signal of azomethine-NH proton was even more influenced by the electronic effects of present substituents than by the weak interactions.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

  • CEP classification

    CC - Organic chemistry

  • OECD FORD branch

Result continuities

  • Project

    <a href="/en/project/GP14-02165P" target="_blank" >GP14-02165P: Red-emitting Fluorescence Sensors Based on Azaphthalocynine Structure: Study of Aza-Crown Recognition Moiety</a><br>

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2016

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Journal of Porphyrins and Phthalocyanines

  • ISSN

    1088-4246

  • e-ISSN

  • Volume of the periodical

    20

  • Issue of the periodical within the volume

    8-11

  • Country of publishing house

    FR - FRANCE

  • Number of pages

    12

  • Pages from-to

    1122-1133

  • UT code for WoS article

    000390248600027

  • EID of the result in the Scopus database

    2-s2.0-84988613824