First preparation of low band gap fulvene-modified polynorbornene via ring-opening metathesis polymerization

Godman, Nicholas P.; Balaich, Gary J.; Iacono, Scott T.

doi:10.1039/c6cc00897f

Cited by 16 publications

(14 citation statements)

References 32 publications

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“…It represents one among the classical nonalternant π-electron systems that potentially satisfy the Huckel 4N + 2 rule [16]. Due to the polarization of the exocyclic double bond, FV shows a strong reactivity towards a large variety of reagents and FV derivatives have been polymerized using different techniques [16,17,18]. A particular FV derivate is dibenzofulvene ( DBF or 9-methylene-9 H -fluorene), in which two benzene rings are symmetrically condensed at two fulvene edges.…”

Section: Introductionmentioning

confidence: 99%

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

et al. 2018

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Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a-h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2 -position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated.

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Section: Introductionmentioning

confidence: 99%

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

et al. 2018

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“…Despite their reactive nature, fulvenes have been successfully used in the formation of several materials, including dynamic polymers (dynamers) [190], hydrogels [191], and precursors to charge-transfer complexes [181,234–235]. Dynamers, referred to as dynamers, are a class of adaptive polymers formed through reversible covalent bonds or noncovalent interactions, allowing continuous modification through bond formation and/or breaking.…”

Section: Reviewmentioning

confidence: 99%

“…Pentafulvenes have also been used to prepare monomers for ring-opening metathesis polymerisation (ROMP) to generate facially amphiphilic polymers [182,235,237–238]. Ilker et al employed the DAC between alkyl pentafulvenes and maleic anhydride to initially prepare norbornene anhydride monomers that could be further functionalised to afford norbornene imide monomers (Scheme 21) [105,237].…”

Section: Reviewmentioning

confidence: 99%

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Swan¹,

Platts²,

Blencowe³

2019

Beilstein J. Org. Chem.

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The unusual electronic properties and unique reactivity of fulvenes have interested researchers for over a century. The propensity to form dipolar structures at relatively low temperatures and to participate as various components in cycloaddition reactions, often highly selectively, makes them ideal for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes. Tables providing comprehensive directories of fulvene cycloaddition chemistry are provided, including fulvene intramolecular and intermolecular cycloadditions complete with reactant partners and their resulting cyclic adducts, which provide a useful reference source for synthetic chemists working with fulvenes and complex polycyclic scaffolds.

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“…Ring‐opening metathesis polymerization (ROMP) has enabled access to a diverse array of polymeric materials . The structural control that has been made possible from well‐defined metal‐based initiators includes a broad scope of monomer classes with diverse functional group tolerance, stereocontrol, sequence specificity, and copolymer constructs . Inspired by the breadth of tunability afforded by metal‐mediated ROMP, we have recently investigated opportunities from an organocatalyzed variant …”

Section: Introductionmentioning

confidence: 99%

Bidirectional metal‐free ROMP from difunctional organic initiators

Alrashdi

Boydston

2017

J. Polym. Sci. Part A: Polym. Chem.

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First preparation of low band gap fulvene-modified polynorbornene via ring-opening metathesis polymerization

Cited by 16 publications

References 32 publications

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Bidirectional metal‐free ROMP from difunctional organic initiators

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