Phosphonium‐ and Borate‐Bridged Zwitterionic Ladder Stilbene and Its Extended Analogues

Fukazawa, Aiko; Yamada, Hiroshi; Yamaguchi, Shigehiro

doi:10.1002/anie.200801834

Cited by 199 publications

(71 citation statements)

References 53 publications

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“…Thus contrasting reactivity is seen for 3 ] (318; Scheme 99), which illustrates both reaction pathways in a single molecule. [164] A related application of such P/B additions has been described by Yamaguchi and co-workers [165] who used the intramolecular addition of phosphines and boranes to make species including 319 that are of interest for electronic materials (Scheme 100).…”

Section: Flp Additions To Alkynesmentioning

confidence: 99%

Frustrated Lewis Pair Chemistry: Development and Perspectives

2015

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Frustrated Lewis pairs (FLPs) are combinations of Lewis acids and Lewis bases in solution that are deterred from strong adduct formation by steric and/or electronic factors. This opens pathways to novel cooperative reactions with added substrates. Small-molecule binding and activation by FLPs has led to the discovery of a variety of new reactions through unprecedented pathways. Hydrogen activation and subsequent manipulation in metal-free catalytic hydrogenations is a frequently observed feature of many FLPs. The current state of this young but rapidly expanding field is outlined in this Review and the future directions for its broadening sphere of impact are considered.

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Section: Flp Additions To Alkynesmentioning

confidence: 99%

Frustrated Lewis Pair Chemistry: Development and Perspectives

2015

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“…[16,17] The materials obtained in the context of our studies, display highly advantageous, unprecedented photophysical properties with respect to emission wavelengths, intensity, and tunability. Since then, the groups of Yamaguchi [18] and Matano, [19] among others, were able to further solidify the benefits of phosphole units within p-conjugated assemblies, reporting materials with remarkable optoelectronic properties. In 2007, Sanji, Shiraishi, and Tanaka reported the first phosphole-cored dendrimers with enhanced emission intensities resulting from an energytransfer (ET) from the branches to the core.…”

Section: Introductionmentioning

confidence: 99%

Dendrimeric Oligo(phenylenevinylene)‐Extended Dithieno[3,2‐b:2′,3′‐d]phospholes—Synthesis, Self‐Organization, and Optical Properties

Romero‐Nieto

Merino

Rodríguez‐López

et al. 2009

Chemistry A European J

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A boost from the branches: Incorporation of the dithieno[3,2-b:2',3'-d]phosphole system as a core in oligo(phenylenevinylene) dendrimers (an example is shown here) provides materials that exhibit energy-transfer features relaying incoming photons from the dendrons towards the core, which in turn shows enhanced emission intensity. The optical properties and self-assembly features of the dendrimers can be impacted by the terminal groups (-H, -CF(3), or -NPh(2)) employed.To establish this system as a fluorescent core in pi-conjugated dendrimers, a series of oligo(phenylenevinylene) (OPV)-extended dithieno[3,2-b:2',3'-d]phospholes has been prepared by means of a Wittig-Horner protocol with a dithienophosphole dialdehyde and appropriately functionalized phosphonates. The "zero-generation" model compounds have provided the general accessibility of OPV-functionalized dithienophospholes, and show varying emission colors covering the optical spectrum from green to red. Expansion of the synthetic strategy towards the corresponding first-generation dendrimers has provided materials that show intriguing self-organization features in case of the phenyl-terminated dendrimer, forming large one-dimensional microfibres, as well as desirable energy-transfer processes from the dendrons to the dithienophoshole core resulting in an enhanced emission intensity for the latter. The present study has revealed that the terminal end-groups of the OPV branches have significant impact on the optical features of the OPV dendrimers as a whole.

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“…These findings illustrate the utility of the FLP strategy in the formation of such heterocycles. It is noteworthy that related intramolecular phosphino-borane additions to alkynes have been elegantly exploited by Yamaguchi and co-workers [37] to effect the formation of heterocyclic zwitterionic phosphonium borate species, which have applications as electronic materials.…”

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confidence: 99%