Discotic liquid crystals of transition metal complexes 51: Synthesis and mesomorphism of flat-pumpkin-shaped phthalocyanine-fullerene dyads

Yoshioka, Miho; Ohta, Kazuchika; Miwa, Yohei; Kutsumizu, Shoichi; Yasutake, Mikio

doi:10.1142/s1088424614500643

Cited by 8 publications

(2 citation statements)

References 39 publications

(73 reference statements)

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“…When such intermolecular interactions are enforced in the solid state by addition of, for example, mesogenic building blocks such as long alkyl chains, Pcs display liquid‐crystalline features. Although many different Pc mesogens, octa‐ or tetra‐substituted derivatives, have been synthesized, there are fewer reports describing liquid‐crystalline phthalocyanine–fullerene (Pc−C 60 ) conjugates, since the incorporation of fullerene into liquid‐crystalline columnar phases requires tedious synthetic efforts …”

Section: Introductionmentioning

confidence: 99%

“…Although many different Pc mesogens, octa-or tetra-substituted derivatives, have been synthesized, [13] there are fewer reports describing liquid-crystalline phthalocyanine-fullerene (PcÀC 60 )c onjugates, since the incorporation of fullerenei nto liquid-crystalline columnar phases requires tedious synthetic efforts. [14][15][16][17][18][19] One of the key structural factorsf or mesomorphic PcÀC 60 conjugates consists of flexible or semiflexibles pacers connecting Pc and C 60 .I na ddition, the simultaneous organization of the electron-donating Pc and the electron-accepting C 60 in mesophases constitutes an appealing strategy towards longrange ambipolar charget ransport properties, which is of relevance for molecular photovoltaics. [16] To the best of our knowledge, there are no literature reports on photoinduced electron transfer in liquid-crystalline PcÀC 60 conjugates nor on their incorporation into photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Electron Transfer in a Zinc Phthalocyanine–Fullerene Conjugate Connected by a Long Flexible Spacer

et al. 2016

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A hexadodecyl‐substituted zinc phthalocyanine covalently linked through a flexible spacer to a fullerene—ZnPc−C60—has been investigated regarding electron transfer from the photoexcited, electron‐donating ZnPc to the electron‐accepting C60. While ground‐state interactions between electron donor and acceptor within ZnPc−C60 could not be detected via steady‐state absorption spectroscopy, clear proof for excited‐state interactions came from steady‐state fluorescence spectroscopy. To this end, the fluorescence in ZnPc−C60 is strongly quenched with quantum yields in THF as low as 0.05. Insight into excited‐state electron‐transfer deactivation within ZnPc−C60 came from time‐resolved femtosecond transient absorption spectroscopy. For example, upon exclusive excitation of the phthalocyanine within the ZnPc−C60 conjugate, a set of transients evolve featuring, on the one hand, the signature of the one‐electron oxidized ZnPc radical cation and, on the other hand, of the one‐electron reduced C60 radical anion. The analysis of the corresponding dynamics in chlorobenzene resulted in lifetimes for charge‐separation and charge‐recombination of 7.4 ps and 2.2 ns, respectively.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinduced Electron Transfer in a Zinc Phthalocyanine–Fullerene Conjugate Connected by a Long Flexible Spacer

et al. 2016

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Fulleren‐gefüllte Flüssigkristall‐Sterne: Ein supramolekularer Klick‐Mechanismus zur Bildung von maßgeschneiderten Donor‐Akzeptor‐Strukturen

et al. 2019

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Zwei formtreue Sternmesogene mit Oligo(phenylenethenylen)-Armen und einem Phthalocyanin-Kern wurden erfolgreich synthetisiert. Dabei stellt eines (2)Freiraum bereit, und das andere (3)i st mit vier Fullerenen, die mittels eines Abstandhalters verbunden sind, sterisch überfrachtet. Im Gegensatz zu einem kleineren diskotischen Derivat (1), bildet Mesogen 2 eine kolumnare flüssigkristalline (LC) Phase aus, die keine p-Stapelung zeigt und nur zum Teil orientiert werden kann, während 3 kein LC ist. Die 1:1-Mischung von 2 und 3 generiert einen außergewçhnlichen, orientierbaren kolumnaren LC mit deutlicher p-Stapelung und einer Fulleren-Quadrupelhelix. Dies ist die Folge eines beispiellosen Klick-Mechanismus,der einem Kugelarretierungs-Mechanismus ähnelt. Die C 60 -Einheiten verbinden dabei auchu nterschiedliche Kolumnen. Dieser Prozess wird durch Nanosegregation und Raumfüllung der Lücken durchd ie Fullerene angetrieben. Photophysikalische Untersuchungen bestätigen das Vorhandensein eines Lichtsammelsystems,w obei sowohl in Lçsung als auchi mF estkçrper ladungsgetrennte Zustände generiert wurden,w as solcheh ochgeordneten Materialien attraktiv für das Studium in zukünftigen photovoltaischen Zellen macht.

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Fullerene‐Filled Liquid‐Crystal Stars: A Supramolecular Click Mechanism for the Generation of Tailored Donor–Acceptor Assemblies

et al. 2019

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Tw os hape-persistent star mesogens with oligo(phenylene ethenylene) arms and ap hthalocyanine core-one providing free space (2)and one sterically encumbered by four fullerenes attached through spacers (3)-have been successfully synthesized. In contrast to the smaller discotic derivative 1,mesogen 2 forms acolumnar liquid crystal (LC), which can only be partially aligned without p-stacking, while 3 is not an LC.E xceptionally,t he 1:1m ixture of 2 and 3 forms an alignable columnar LC with strong p-stacking and quadruply helically organized fullerenes by an unprecedented click process that is similar to ab all detent mechanism. The C 60 units also interconnect different columns.T his is driven by nanosegregation and space-filling of the voids with fullerenes. Photophysical studies confirm the presence of alight-collecting system that generates charge-separated states in solution and in the solid state,w hichm akes such highly organized materials attractive for the study of future photovoltaic devices.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Discotic liquid crystals of transition metal complexes 51: Synthesis and mesomorphism of flat-pumpkin-shaped phthalocyanine-fullerene dyads

Abstract: ABSTRACT:We have synthesised a novel type of donor-acceptor liquid crystalline material, phthalocyanine-fullerene (Pc-C 60 ) dyad, [m, p, m'-(C 14 O) 3 PhO] 6 PcCu-C 60 (7), and the Pc precursors, [m, p, m'-(C 14 O) 3 PhO] 6 PcCu-OFBA (6) and [m, p, m'-(C 14

Cited by 8 publications

References 39 publications

Photoinduced Electron Transfer in a Zinc Phthalocyanine–Fullerene Conjugate Connected by a Long Flexible Spacer

Photoinduced Electron Transfer in a Zinc Phthalocyanine–Fullerene Conjugate Connected by a Long Flexible Spacer

Fulleren‐gefüllte Flüssigkristall‐Sterne: Ein supramolekularer Klick‐Mechanismus zur Bildung von maßgeschneiderten Donor‐Akzeptor‐Strukturen

Fullerene‐Filled Liquid‐Crystal Stars: A Supramolecular Click Mechanism for the Generation of Tailored Donor–Acceptor Assemblies

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