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A Cycloparaphenylene Acetylene as Potential Precursor for an Armchair Carbon Nanotube

Sidler, Eric; Röthlisberger, Ramon; Mayor, Marcel 1
1 Institut für Nanotechnologie (INT), Karlsruher Institut für Technologie (KIT)

Abstract:

The bottom-up synthesis of carbon nanotubes (CNTs) is a long-standing goal in synthetic chemistry. Producing CNTs with defined lengths and diameters would render these materials and thus their fascinating properties accessible in a controlled way. Inspired by a recently reported synthesis of armchair graphene sheets that relied on a benzannulation and Scholl oxidation of a poly(p-phenylene ethynylene), the same strategy is applied on a cyclic substrate with a short, but well defined CNT as target structure. Herein we report the synthesis of a derivatized [12]cycloparaphenylene acetylene ([12]CPPA) that was accessible employing a Sonogashira macrocyclization. The obtained macrocycle is the largest [n]CPPA reported to date and displays bright turquoise fluorescence with a large quantum yield of 77 %. The [12]CPPA can be transformed by a 12-fold benzannulation that converts each alkyne to a naphthalene and therefore allows formation of an armchair [12,12]CNT precursor. The final 72-fold Scholl oxidation to the [12,12]CNT turned out to be challenging and its optimization requires an improved synthetic strategy to produce large quantities of the final precursor. ... mehr

Zugehörige Institution(en) am KIT Institut für Nanotechnologie (INT)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 10.12.2024
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000176834
HGF-Programm 43.32.01 (POF IV, LK 01) Molecular Materials Basis for Optics & Photonics
Erschienen in Chemistry – A European Journal
Verlag John Wiley and Sons
Band 30
Heft 69
Seiten ArtNr. 202403084
Vorab online veröffentlicht am 03.11.2024
Nachgewiesen in Dimensions
Scopus
OpenAlex
Web of Science

Verlagsausgabe §
DOI: 10.5445/IR/1000176834
Veröffentlicht am 06.12.2024
Seitenaufrufe: 25
seit 06.12.2024
Downloads: 13
seit 11.12.2024
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