Application of conducting polymers as catalysts for cis-trans photoisomerization of alkenes

Yanagida, Shozo; Hanazawa, Makoto; Kabumoto, Akira; Pac, Chyongjin; Yoshino, Katsumi

doi:10.1016/0379-6779(87)90979-9

Cited by 5 publications

(4 citation statements)

References 5 publications

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“…In order to further investigate the phenomenon, samples at different polymerization times were prepared and analyzed to clarify Figure 1 Chemical polymerization of thiophene using FeCl 3 as oxidant. 13 Toward a trace-free oxidant-PTTh polymerization C Ong et al if there would be any change in the properties of PTTh produced with different polymerization times, that is, 3 and 16.5 h. These times were chosen to produce two polymers corresponding to the time when (3 h) and long after (16.5 h) the Fe(III) oxidant was 'used up' according to equation (1). Elemental analysis of the samples showed the ratio of C:H:S 4.3:3.1:1 and 4.2:2.6:1 for 3 h and 16.5 h, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Combining the results, a few hypotheses can be made: first, during initial VPP, oxidized PTTh is formed, which has a ordered structure owing to Fe(III)PTS templating. Second, this occurs with Fe(III) as the oxidation agent as per usual understanding according to equation (1). Last, with continued polymerization, when the Fe(III) oxidant is 'used up' according to equation (1), a reduced and nontemplated, less-ordered form of PTTh is formed.…”

Section: Resultsmentioning

confidence: 99%

“…This ratio has also been seen in electropolymerization and oxidative chemical polymerization, where at least 2 mol of electrons (oxidant) are required to produce 1 mol of polymer. 10,13,14 In this report, measurement of the masses of iron(III) paratoluenesulfonate (Fe(III)PTS) oxidant used and polymer produced during chemical VPP of TTh showed that more polymer was produced than expected according to equation (1). In other words, the molar amount of polymer produced was more than half the molar amount of oxidant.…”

Section: Introductionmentioning

confidence: 85%

“…Intrinsically conducting polymers (ICPs) are currently being intensively researched, not only for their conductivity but also for their unique properties such as their ability to work in catalytic, electrochromic and light harvesting applications. [1][2][3][4][5][6] Polythiophene is one ICP recognized for its high stability and tunable properties. By attaching different side groups to polythiophene, polymers with different band gaps and solubilities can be obtained, making it suitable for a wide range of applications.…”

Section: Introductionmentioning

confidence: 99%

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Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Ong

Bayley

Winther‐Jensen

et al. 2012

Polym J

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Vapor phase polymerization (VPP) of conducting polymers has been widely reported as a versatile technique to obtain thin films with high conductivity and order. One oxidant commonly used for VPP is iron(III) para-toluenesulfonate (Fe(III)PTS) owing to its outstanding film-forming properties. The polymerization mechanism using Fe(III)PTS has been believed to follow the normal route, where (at least) two Fe(III) is needed for oxidizing one monomer unit to form the polymer. Surprisingly, when polymerizing terthiophene (TTh) monomers at 100 1C using Fe(III)PTS, it was found that B2.3 times more the expected amount of PTTh was produced, when long polymerization times were used. An explanation for the phenomenon was found when VPP of TTh was successful using only para-toluenesulfonic acid (PTSa) as oxidant. It is believed that PTSa is gradually converted to SO 3 and toluene at elevated temperature and that reduction of SO 3 is driving the oxidation of the TTh monomers. This finding also opens a useful oxidative polymerization route where the oxidant can be converted to volatile compounds leaving no trace in the end product.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 85%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Ong

Bayley

Winther‐Jensen

et al. 2012

Polym J

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Conjugated Polymers as Photoredox Catalysts: Visible‐Light‐Driven Reduction of Aryl Aldehydes by Poly(p‐phenylene)

2012

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The use of visible light in photocatalysis has been intensively studied because of its natural abundance, ease of use, and promising potential for industrial applications. However, there are several challenges to utilizing visible light for organic functional group transformations. These challenges include the low absorptivity of most organic compounds in the visible spectrum, and side reactions are often prevalent in photochemical reactions. Visible‐light‐sensitive catalysts offer a means to overcome these obstacles. Conjugated polymers are semiconductors that offer a large range of redox potentials, they are stable, and they often absorb visible light. Despite these desirable properties for photocatalysis, only a limited number of organic reactions utilizing conjugated polymers as photocatalysts have been reported. In one such example, poly(p‐phenylene) was used to induce the pinacol coupling reaction of benzaldehyde upon irradiation with visible light. In this work, visible light, thiols, and poly(p‐phenylene) were employed to reduce aryl aldehydes to their respective alcohols to better characterize the reaction mechanisms of this system. The effects of varying reaction conditions on the rate of photocatalysis indicated interfacial electron transfer from the poly(p‐phenylene) surface to the substrate as the initial productive step. Additionally, the chemoselective reduction of aryl aldehydes over aryl ketones and alkyl aldehydes was achieved with this system.

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Efficient visible-light-driven photocatalysis. Poly(pyridine-2,5-diyl)-catalysed hydrogen photoevolution and photoreduction of carbonyl compounds

Matsuoka¹,

Kohzuki²,

Nakamura³

et al. 1991

J. Chem. Soc., Chem. Commun.

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Application of conducting polymers as catalysts for cis-trans photoisomerization of alkenes

Cited by 5 publications

References 5 publications

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Toward a trace-free oxidant—insight into unexpected high yields of vapor phase polymerized polyterthiophene

Conjugated Polymers as Photoredox Catalysts: Visible‐Light‐Driven Reduction of Aryl Aldehydes by Poly(p‐phenylene)

Efficient visible-light-driven photocatalysis. Poly(pyridine-2,5-diyl)-catalysed hydrogen photoevolution and photoreduction of carbonyl compounds

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