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pH-Sensitive subphthalocyanines and subazaphthalocyanines.

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Title: pH-Sensitive subphthalocyanines and subazaphthalocyanines.
Authors: Skvortsov, Ivan A.1,2 (AUTHOR), Zimcik, Petr2 (AUTHOR), Stuzhin, Pavel A.1 (AUTHOR) stuzhin@isuct.ru, Novakova, Veronika2 (AUTHOR) veronika.novakova@faf.cuni.cz
Source: Dalton Transactions: An International Journal of Inorganic Chemistry. 8/28/2020, Vol. 49 Issue 32, p11090-11098. 9p.
Subjects: Microemulsions, Photoinduced electron transfer, Molecular recognition, Phenoxy groups, Polyethylene terephthalate, Trifluoroacetic acid
Abstract: Although subphthalocyanines (SubPcs) possess advantageous fluorescence properties and serve as an amazing tool to attach a recognition sensor moiety to the axial position, a limited number of switchable SubPcs have been described so far. Isosteric aza-replacement is known to improve sensing properties in closely related phthalocyanine families; however, pyrazino[2,3-b,g,l]subporphyrazines (SubPyzPzs) have not yet been investigated for use in sensing applications. Therefore, this project focuses on the synthesis and sensing abilities of pH-sensitive SubPcs and SubPyzPzs on the principle of photoinduced electron transfer (PET). 4-Dimethylaminophenoxy (for acidic pH) or 4-hydroxyphenoxy (for basic pH) groups were employed as pH-sensitive axial ligands. Electrochemical studies revealed improvements in the electron-accepting properties of SubPyzPzs (Ered −0.56 V vs. SCE) in comparison to those of SubPcs (Ered −1.0 V vs. SCE). Hydroxy groups on the axial phenoxy ligands of SybPyzPzs and SubPcs have been found to act as donors for PET. The sensing properties under basic conditions could not be studied, since all the SubPcs and SubPyzPzs decomposed under basic conditions, SubPyzPzs were more susceptible to this process. On the other hand, compounds with 4-dimethylaminophenoxy groups as axial ligands showed great potential for sensing applications. These compounds were nonfluorescent (ΦF < 0.01) in acetone due to efficient PET, while their fluorescence steeply increased by two orders of magnitude upon the addition of trifluoroacetic acid, reaching a ΦF value of up to 0.17 (λem range of 563–590 nm). These compounds maintained their sensing properties in aqueous medium after incorporation into microemulsions. The most basic derivative showed pKA = 2.95 with ΦF = 0.10 in the ON state (fluorescence enhancement factor = 46, λem = 577 nm). [ABSTRACT FROM AUTHOR]
Copyright of Dalton Transactions: An International Journal of Inorganic Chemistry is the property of Royal Society of Chemistry and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: pH-Sensitive subphthalocyanines and subazaphthalocyanines.
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  Data: &lt;searchLink fieldCode=&quot;AR&quot; term=&quot;%22Skvortsov%2C+Ivan+A%2E%22&quot;&gt;Skvortsov, Ivan A.&lt;/searchLink&gt;&lt;relatesTo&gt;1,2&lt;/relatesTo&gt; (AUTHOR)&lt;br /&gt;&lt;searchLink fieldCode=&quot;AR&quot; term=&quot;%22Zimcik%2C+Petr%22&quot;&gt;Zimcik, Petr&lt;/searchLink&gt;&lt;relatesTo&gt;2&lt;/relatesTo&gt; (AUTHOR)&lt;br /&gt;&lt;searchLink fieldCode=&quot;AR&quot; term=&quot;%22Stuzhin%2C+Pavel+A%2E%22&quot;&gt;Stuzhin, Pavel A.&lt;/searchLink&gt;&lt;relatesTo&gt;1&lt;/relatesTo&gt; (AUTHOR)&lt;i&gt; stuzhin@isuct.ru&lt;/i&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;AR&quot; term=&quot;%22Novakova%2C+Veronika%22&quot;&gt;Novakova, Veronika&lt;/searchLink&gt;&lt;relatesTo&gt;2&lt;/relatesTo&gt; (AUTHOR)&lt;i&gt; veronika.novakova@faf.cuni.cz&lt;/i&gt;
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  Data: Although subphthalocyanines (SubPcs) possess advantageous fluorescence properties and serve as an amazing tool to attach a recognition sensor moiety to the axial position, a limited number of switchable SubPcs have been described so far. Isosteric aza-replacement is known to improve sensing properties in closely related phthalocyanine families; however, pyrazino[2,3-b,g,l]subporphyrazines (SubPyzPzs) have not yet been investigated for use in sensing applications. Therefore, this project focuses on the synthesis and sensing abilities of pH-sensitive SubPcs and SubPyzPzs on the principle of photoinduced electron transfer (PET). 4-Dimethylaminophenoxy (for acidic pH) or 4-hydroxyphenoxy (for basic pH) groups were employed as pH-sensitive axial ligands. Electrochemical studies revealed improvements in the electron-accepting properties of SubPyzPzs (Ered −0.56 V vs. SCE) in comparison to those of SubPcs (Ered −1.0 V vs. SCE). Hydroxy groups on the axial phenoxy ligands of SybPyzPzs and SubPcs have been found to act as donors for PET. The sensing properties under basic conditions could not be studied, since all the SubPcs and SubPyzPzs decomposed under basic conditions, SubPyzPzs were more susceptible to this process. On the other hand, compounds with 4-dimethylaminophenoxy groups as axial ligands showed great potential for sensing applications. These compounds were nonfluorescent (ΦF &lt; 0.01) in acetone due to efficient PET, while their fluorescence steeply increased by two orders of magnitude upon the addition of trifluoroacetic acid, reaching a ΦF value of up to 0.17 (λem range of 563–590 nm). These compounds maintained their sensing properties in aqueous medium after incorporation into microemulsions. The most basic derivative showed pKA = 2.95 with ΦF = 0.10 in the ON state (fluorescence enhancement factor = 46, λem = 577 nm). [ABSTRACT FROM AUTHOR]
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  Data: &lt;i&gt;Copyright of Dalton Transactions: An International Journal of Inorganic Chemistry is the property of Royal Society of Chemistry and its content may not be copied or emailed to multiple sites without the copyright holder&#39;s express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.&lt;/i&gt; (Copyright applies to all Abstracts.)
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RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1039/d0dt01703e
    Languages:
      – Code: eng
        Text: English
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      Pagination:
        PageCount: 9
        StartPage: 11090
    Subjects:
      – SubjectFull: Microemulsions
        Type: general
      – SubjectFull: Photoinduced electron transfer
        Type: general
      – SubjectFull: Molecular recognition
        Type: general
      – SubjectFull: Phenoxy groups
        Type: general
      – SubjectFull: Polyethylene terephthalate
        Type: general
      – SubjectFull: Trifluoroacetic acid
        Type: general
    Titles:
      – TitleFull: pH-Sensitive subphthalocyanines and subazaphthalocyanines.
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            NameFull: Skvortsov, Ivan A.
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            NameFull: Zimcik, Petr
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            NameFull: Stuzhin, Pavel A.
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            NameFull: Novakova, Veronika
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            – D: 28
              M: 08
              Text: 8/28/2020
              Type: published
              Y: 2020
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