Synthesis and electronic properties of bridged [8]-, [12]- and [16]-cyclo-para-phenylenes

Autor: Fabien Lucas, Joëlle Rault-Berthelot, Cassandre Quinton, Cyril Poriel
Přispěvatelé: Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), European Union [699648], Region Bretagne (DIADEM project), GENCI [AD010805032R1], European Project: 699648,H2020,H2020-MSCA-IF-2015,FRODO(2016)
Rok vydání: 2022
Předmět:
Zdroj: Journal of Materials Chemistry C
Journal of Materials Chemistry C, 2022, 10, pp.14000-14009. ⟨10.1039/d2tc00881e⟩
ISSN: 2050-7534
2050-7526
DOI: 10.1039/d2tc00881e
Popis: International audience; Hoop-shaped pi-conjugated macrocycles constitute a new family of pi-conjugated systems displaying unique properties induced by their radially directed pi-orbitals. The electronic properties of these nanohoops are deeply dependent on their budding units and their size. We report herein the first size dependence study of [8]-, [12]- and [16] cyclo-para-phenylenes bridged by nitrogen atoms. The properties were elucidated by H-1 NMR, cyclic voltammetry, UV-vis absorption and fluorescence spectroscopy (in solution and in thin film). Thus, this work reports one of the largest bridged nanohoops synthesized, namely [4]cyclo-para-9-ethylhexyl-2,7-diphenyl-carbazole [16]CPP4N, an analog of [16]CPP, which displays an alternation of four unbridged biphenylenes and four nitrogen bridged biphenylenes. Removing either all the unbridged phenylenes ([4]cyclo-para-9-ethylhexyl-carbazole [8]CPP4N, an analog of [8]CPP) or one budding unit ([3]cyclo-para-9-ethylhexyl-2,7-diphenyl-carbazole [12]CPP3N, an analog of [12]CPP) allows decreasing the size of the nanohoop with nevertheless drastically different consequences on the properties. This is what we aim at reporting in this work.
Databáze: OpenAIRE
Externí odkaz: