Synthesis and Properties of Porphyrin Nanotubes

Discrete π‐conjugated zinc porphyrin nanotubes are investigated as molecular analogues of carbon nanotubes. These porphyrin nanotubes have a diameter of 2.4 nm (Zn–Zn distance) and lengths of up to 3.6 nm, measured to the van der Waals surfaces of the outer β‐pyrrole hydrogen atoms, or 4.5 nm measur...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 102; no. 1
Main Authors Haver, Renée, Anderson, Harry L.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.01.2019
Wiley Subscription Services, Inc
Subjects
Absorption spectra
Aromatic compounds
Carbon nanotubes
Chemistry
Chemistry, Multidisciplinary
Conjugation
Coupling (molecular)
Fluorescence
Hydrogen atoms
Nanotechnology
Nanotubes
Oligomers
Para hydrogen
Physical Sciences
pi-conjugation
porphyrins
Rigidity
Science & Technology
supramolecular chemistry
Synthesis
template-directed synthesis
Zinc
template-directed synthesis
EXCITED-STATE PHOTODYNAMICS
DELOCALIZATION
MOLECULAR SQUARE
porphyrins
CARBON NANOTUBES
ALL-CARBON
ARRAYS
OLIGOMERS
nanotubes
pi-conjugation
GROWTH
SUPRAMOLECULAR INTERACTIONS
supramolecular chemistry
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Summary:Discrete π‐conjugated zinc porphyrin nanotubes are investigated as molecular analogues of carbon nanotubes. These porphyrin nanotubes have a diameter of 2.4 nm (Zn–Zn distance) and lengths of up to 3.6 nm, measured to the van der Waals surfaces of the outer β‐pyrrole hydrogen atoms, or 4.5 nm measured to the para hydrogen atoms of the aryl groups. We explore three different strategies for synthesizing these nanotubes. The first two strategies use a template to achieve direct or sequential stave‐joining, respectively, and proceed via linear oligomers that pre‐define the length of the nanotube. These strategies are applied to synthesize porphyrin nanotubes containing 12‐ or 18‐porphyrin subunits, with ethynylene (C2) or butadiynylene (C4) links between the 6‐porphyrin nanorings. The third strategy involves the covalent stacking of pre‐formed 6‐porphyrin nanorings to form a 12‐porphyrin nanotube, without using a template to guide this coupling reaction. The nanotubes show strongly red‐shifted absorption spectra and low fluorescence quantum yields, indicating structural rigidity and extensive π‐conjugation.
Bibliography:Dedicated to
on the occasion of his retirement
François Diederich
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.201800211