Synthesis, characterization and ethanol sensing properties of carboxylic acid-terminated naphthoxy substituted phthalocyanines

Seher Neccaroğlu Işık, Gülnur Keser Karaoğlan, Birsel Can Ömür, Ahmet Altındal, Gülşah Gümrükçü Köse*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


A new mono substituted phthalonitrile derivative of 4-(6-carboxy-2-naphthoxy)phthalonitrile was prepared by a nucleophilic displacement reaction of 4-nitrophthalonitrile with 6-hydroxy-2-naphthoic acid. Metallophthalocyanines of [2,9,16,23-tetra-(4-(6-carboxy-2-naphthoxy)-phthalocyaninato-zinc(II)], cobalt(II), copper(II), nickel (II), and metal free phthalocyanines bearing carboxylic acid groups at the peripheral positions have been designed and synthesized by cyclotetramerisation of the phthalonitrile to investigate the influence of the central metal atom on the ethanol vapor sensing properties. All newly synthesized compounds were characterized by UV–Vis, FTIR, 1H-NMR, MALDI-TOF MS and elemental analysis spectral data. The influence of COOH group on the organic vapor sensing performance towards 5 different groups of analytes (alkanes, chlorinated hydrocarbons, amines, alcohols and aromatics) were examined. Ethanol adsorption onto the thin films of these compounds and the effects of operating temperature on the sensing properties were also studied. The sensing data show that all the films of phthalocyanine compounds show response to ethanol, among which, [2,9,16,23-tetra-(4-(6-carboxy-2-naphthoxy)-phthalocyaninato-nickel (II)] based sensor show the highest response, demonstrating central metal atom dependence of ethanol sensitivity. Surface topography of the sensing films were analyzed by atomic force microscopy.

Original languageEnglish
Pages (from-to)7-15
Number of pages9
JournalSynthetic Metals
Publication statusPublished - Dec 2018
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2018 Elsevier B.V.


This study was supported by the Research Fund of Yildiz Technical University (Project No.: FDK-2017-3039 ).

FundersFunder number
Yildiz Teknik ÜniversitesiFDK-2017-3039


    • Carboxylic acid
    • Ethanol sensing
    • Naphthol
    • Phthalocyanine
    • Response time
    • Sensitivity


    Dive into the research topics of 'Synthesis, characterization and ethanol sensing properties of carboxylic acid-terminated naphthoxy substituted phthalocyanines'. Together they form a unique fingerprint.

    Cite this