CycloParaPhenylenes ([n]CPPs) are fully conjugated macrocycles constituted by n para-linked benzene units (Figure), which exhibit size-dependent optical and electronic proprieties [1,2]. [n]CPPs exhibit the narrowing of the HOMO-LUMO gap as the number of aromatic units decreases, consequently, the emission spectra of CPP derivatives are blue-shifted and quantum efficiency increases as the macrocycle become larger [2]. This optoelectronic properties make the [n]CPPs excellent candidates for applications in nanoelectronics and photonics. [n]Cycloparaphenylene (carbon nanorings) are considered as potential templates for the bottom-up synthesis of uniform single wall carbon nanotubes [3]. Differently by other macrocycles, such as calixarenes, pillararenes and resorcinarenes, the recognition properties of [n]CPP macrocycles have been scarcely investigated and the few examples in the literature mainly regarded the complexation of fullerenes [4,5]. In the present work, we have designed and synthesized the [8]CPP derivative 1 bearing a 1,4-dimetoxybenzene electron-rich moiety which is considered as useful supramolecular synthon able to interact with cationic electron-poor pyridinium guests. We wish to describe here the synthesis of the 1,4- dimethoxybenzene-incorporating [8]CPP 1 derivative (Figure) the its optical and electronic properties. Finally, for the first time we report here on the molecular recognition abilities of a [8]CPP derivative towards pyridinium guests (Figure) [6].
Recognition of Pyridinium Guests by [8]Cycloparaphenylene Host
DELLA SALA, PAOLO;TALOTTA, CARMEN;DI BENEDETTO, GIUSEPPINA;CARUSO, Tonino;DE ROSA, Margherita;NERI, Placido;GAETA, CARMINE
2017-01-01
Abstract
CycloParaPhenylenes ([n]CPPs) are fully conjugated macrocycles constituted by n para-linked benzene units (Figure), which exhibit size-dependent optical and electronic proprieties [1,2]. [n]CPPs exhibit the narrowing of the HOMO-LUMO gap as the number of aromatic units decreases, consequently, the emission spectra of CPP derivatives are blue-shifted and quantum efficiency increases as the macrocycle become larger [2]. This optoelectronic properties make the [n]CPPs excellent candidates for applications in nanoelectronics and photonics. [n]Cycloparaphenylene (carbon nanorings) are considered as potential templates for the bottom-up synthesis of uniform single wall carbon nanotubes [3]. Differently by other macrocycles, such as calixarenes, pillararenes and resorcinarenes, the recognition properties of [n]CPP macrocycles have been scarcely investigated and the few examples in the literature mainly regarded the complexation of fullerenes [4,5]. In the present work, we have designed and synthesized the [8]CPP derivative 1 bearing a 1,4-dimetoxybenzene electron-rich moiety which is considered as useful supramolecular synthon able to interact with cationic electron-poor pyridinium guests. We wish to describe here the synthesis of the 1,4- dimethoxybenzene-incorporating [8]CPP 1 derivative (Figure) the its optical and electronic properties. Finally, for the first time we report here on the molecular recognition abilities of a [8]CPP derivative towards pyridinium guests (Figure) [6].I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
