Synthesis and Properties of a Chiroptically Active Oligomer from 3,4-Ethylenedioxythiophene and (–)-Myrtenal

Kawashima, Hirotsugu; Goto, Hiromasa

doi:10.3390/ma4061013

Cited by 2 publications

(2 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…CC is another monocyclic conjugated aldehyde with three methyl substituents in the proximity of the polymerizable carbonyl group and is convertible from citral, − an acyclic conjugated aldehyde existing in lemongrass oil . However, there are no examples of the addition polymerization of these monomers, although a polycondensation using myrtenal was recently reported …”

Section: Introductionmentioning

confidence: 99%

New Degradable Alternating Copolymers from Naturally Occurring Aldehydes: Well-Controlled Cationic Copolymerization and Complete Degradation

et al. 2012

View full text Add to dashboard Cite

Three naturally occurring conjugated aldehydes, (1R)-(−)-myrtenal, (S)-(−)-perillaldehyde, and β-cyclocitral, were cationically copolymerized with isobutyl vinyl ether using the EtSO3H/GaCl3 initiating system in the presence of 1,4-dioxane as an added Lewis base. Alternating copolymerization proceeded exclusively via 1,2-carbonyl addition of the aldehydes. In addition, controlled alternating copolymerization was achieved under appropriate reaction conditions, producing copolymers with controlled molecular weights and narrow molecular weight distributions. The relationships between the copolymerization behaviors and the cyclic side group structures of the aldehydes suggested that conjugated and bicyclic structures were important factors for controlled alternating copolymerization. However, too much bulkiness around the carbonyl group resulted in termination of copolymerization. The resulting alternating copolymers were stable under neutral and basic conditions. In sharp contrast, mild acidic conditions degraded the alternating copolymers almost selectively to conjugated aldehydes with low molecular weights as nearly single products.

show abstract

Section: Introductionmentioning

confidence: 99%

New Degradable Alternating Copolymers from Naturally Occurring Aldehydes: Well-Controlled Cationic Copolymerization and Complete Degradation

et al. 2012

View full text Add to dashboard Cite

show abstract

“…In order to improve its solubility, alkyl chains are often introduced as side groups. Also, chiral side chains should induce main chain chirality in conjugated polymers . In this study, we introduced bornyl group as a chiral side chain.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Properties, and Doping Behavior of Optically Active Polythiophenes Bearing a Bornyl Group

Matsumura

Kawabata

Goto

2015

Macro Chemistry & Physics

Self Cite

View full text Add to dashboard Cite

Polythiophenes bearing a bornyl group as a side chain are synthesized. The polymers, which consist of multiple thiophenes and a substituted aromatic ring in the repeat unit, demonstrate right‐handed helicity in the film state. Results of energy level measurements show good agreement with the density functional theory calculation results for the model compounds. In situ electron spin resonance (ESR) studies indicate that increasing the number of unsubstituted thiophene units in the repeat unit increases susceptibility for the dopants. The chiral charge carriers are confirmed with ESR and circular dichroism spectroscopy measurements.

show abstract

Synthesis and Properties of a Chiroptically Active Oligomer from 3,4-Ethylenedioxythiophene and (–)-Myrtenal

Cited by 2 publications

References 39 publications

New Degradable Alternating Copolymers from Naturally Occurring Aldehydes: Well-Controlled Cationic Copolymerization and Complete Degradation

New Degradable Alternating Copolymers from Naturally Occurring Aldehydes: Well-Controlled Cationic Copolymerization and Complete Degradation

Synthesis, Properties, and Doping Behavior of Optically Active Polythiophenes Bearing a Bornyl Group

Contact Info

Product

Resources

About