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Chidawanyika, Wadzanai, and Tebello Nyokong. Carbon 48.10 (2010): 2831-2838.
Amine-functionalized single-walled carbon nanotubes (SWCNTs) were utilized for the covalent attachment of a low-symmetry phthalocyanine derivative through amide bond formation, enabling the synthesis of a novel ZnPc-SWCNT-linked conjugate. This functionalization strategy is based on a diazonium-mediated introduction of amine groups onto the SWCNT surface, which allows for subsequent coupling with carboxylic acid-containing molecules.
In this study, the phthalocyanine complex Tris[9(10),16(17),23(24)-(4-2-mercaptopyridine)-2-(4-carboxyphenoxy]phthalocyaninato zinc(II) (complex 1) was activated with dicyclohexylcarbodiimide (DCC) in DMF under nitrogen to generate a reactive carbodiimide intermediate. Following a 24-hour activation period, amine-functionalized SWCNTs were introduced to the reaction mixture and allowed to react for an additional 48 hours at room temperature. The product was isolated by repeated DMF washing and centrifugation, and oven-dried to yield a black-green ZnPc-SWCNT powder.
The covalent ZnPc-SWCNT conjugate is of significant interest in optoelectronic and sensing applications, where strong electronic coupling between the SWCNT backbone and photoactive ZnPc units is desirable. The use of amine-functionalized SWCNTs ensures site-specific and stable bonding, providing a robust platform for functional nanomaterial development.
This work demonstrates the efficiency of amine-functionalized SWCNTs in forming stable conjugates with complex aromatic systems via amide bond chemistry, expanding their applicability in advanced material synthesis.
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