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説明:

Subphthalocyanines (SubPcs) and their aza-analogues (SubTPyzPz) are fluorophores with strong orange fluorescence emission, however, their sensing ability towards metal cations remains uncharted. To fill this gap, we have developed an efficient method for introducing aza-crown moieties at the axial position of SubPcs and SubTPyzPzs to investigate the structure-activity relationship for sensing of alkali (Li+, Na+, K+) and alkaline earth metal (Ca2+, Mg2+, Ba2+) cations. SubPcs showed better photostability than SubTPyzPzs and even commonly utilized dye, 6-carboxyfluorescein. Selectivity toward metal cations was driven by the size of an aza-crown, irrespective of the counter anion. The stoichiometry of binding was found to be 1:1 in all cases, and interaction between SubPcs and cations was characterized by corresponding apparent binding constants (Ka). Notably, an unusually strong interaction of all sensoric SubPcs with Ba2+ compared to other studied cations was demonstrated. The role of surrounding environment, i.e. the addition of water or methanol, for sensing cations is shown in detail as well. Selectivity towards K+ over Na+ was demonstrated in aqueous media with SubPcs bearing 1-aza6-crown-18 moiety in Tween 80 micelles. In this case, a 5-fold increase of fluorescence quantum yield was observed upon binding K+ ions. The high brightness, photostability, and sensing activity in aqueous media make SubPcs macrocycles promising fluorophores for metal cation sensing.

権利情報:

• Creative Commons BY-NC Attribution-NonCommercial 4.0 International
  

キーワード: sensing, metal cations, host-guest complex, subphthalocyanine, fluorescence, aqueous media

刊行年月日: 2024-01-04

出版者: Royal Society of Chemistry (RSC)

掲載誌:

• Dalton Transactions (ISSN: 14779234) p. 2635-2644

研究助成金:

• Grantová Agentura České Republiky 21-14919J
• Russian Foundation for Basic Research 20-53-26004
• Univerzita Karlova v Praze SVV 260 666
• Univerzita Karlova v Praze PRIMUS/20/SCI/013

原稿種別: 出版者版 (Version of record)

MDR DOI:

公開URL: https://doi.org/10.1039/d3dt03839d

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更新時刻: 2024-08-19 16:30:34 +0900

MDRでの公開時刻: 2024-08-19 16:30:34 +0900