Unprecedented 1,3-Dipolar Cycloaddition: From 1,4,5,8-Naphthalene Bisimides to a New Heterocyclic Skeleton

Gryko, Daniel T.; Rogacki, Maciej K.; Klajn, Jan; Gałęzowski, Michał; Stępień, Dorota K.; Cyrański, Michał K.

doi:10.1021/ol1005032

Cited by 17 publications

(13 citation statements)

References 29 publications

(14 reference statements)

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“…Examples of this are the 1,3-dipolar cycloaddition at the NDI core reported by Gryko et al [61] and the synthesis of a 2,7-core-dialkylated derivative by Marks, Wasielewski, and co-workers. A 1:1 mixture of 2,6-and 2,7-core-dialkylated NDI derivatives was obtained without any regiocontrol in this ruthenium-catalyzed reaction of a core-unsubstituted NDI derivative with styrene; however, this mixture could subsequently be separated by HPLC.…”

Section: Substitution At Core-unsubstituted Ndimentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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Naphthalene diimides, which have for a long time been in the shadow of their higher homologues the perylene diimides, currently belong to the most investigated classes of organic compounds. This is primarily due to the initial synthetic studies on core functionalization that were carried out at the beginning of the last decade, which facilitated diverse structural modifications of the naphthalene scaffold. Compounds with greatly modified optical and electronic properties that can be easily and effectively modulated by appropriate functionalization were made accessible through relatively little synthetic effort. This resulted in diverse interesting applications. The electron-deficient character of these compounds makes them highly valuable, particularly in the field of organic electronics as air-stable n-type semiconductors, while absorption bands over the whole visible spectral range through the introduction of core substituents enabled interesting photosystems and photovoltaic applications. This Review provides an overview on different approaches towards core functionalization as well as on synthetic strategies for the core expansion of naphthalene diimides that have been developed mainly in the last five years.

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Section: Substitution At Core-unsubstituted Ndimentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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“…In fact, only a few examples are known where core‐unsubstituted NDI derivatives were applied as starting compounds for core substitution. Examples of this are the 1,3‐dipolar cycloaddition at the NDI core reported by Gryko et al 61. and the synthesis of a 2,7‐core‐dialkylated derivative by Marks, Wasielewski, and co‐workers.…”

Section: Core‐substituted Naphthalene Diimidesmentioning

confidence: 99%

Sulfoxide‐Directed Metal‐Free ortho‐Propargylation of Aromatics and Heteroaromatics

Eberhart

Shrives

Álvarez

et al. 2015

Chemistry A European J

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A sulfoxide-directed, metal-free ortho-propargylation of aromatics and heteroaromatics exploits intermolecular delivery of a propargyl nucleophile to sulfur followed by an intramolecular relay to carbon. The operationally simple cross-coupling procedure is general, regiospecific with regard to the propargyl nucleophile, and shows complete selectivity for products of ortho-propargylation over allenylation. The use of secondary propargyl silanes allows metal-free ortho-coupling to form carbon–carbon bonds between aromatic and heteroaromatic rings and secondary propargylic centres. The ‘safety-catch’ nature of the sulfoxide directing group is illustrated in a selective, iterative double cross-coupling process. The products of propargylation are versatile intermediates and they have been readily converted into substituted benzothiophenes.

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“…Another example of core‐modified NDI derivatives treats N , N ‐dialkyl NDIs with azomethine ylides through double 1,3‐dipolar cycloadditions and a unique rearrangement that yields to the formation of complex reduced form of the NDI (Scheme ) . It is postulated that the ylide, prepared in boiling toluene with sarcosine and paraformaldehyde, undergoes a 1,3‐dipolar cycloaddition with the NDI acting as dipolarophile forming the intermediate 119 (Scheme ).…”

Section: Core Modification Of Ndismentioning

confidence: 99%

“…Another example of core-modified NDI derivatives treats N,N-dialkyl NDIs with azomethine ylides through double 1,3-dipolar cycloadditions and au nique rearrangementt hat yields to the formation of complex reduced form of the NDI (Scheme 16). [62] It is postulated that the ylide, prepared in boiling toluenew ith sarcosine and paraformaldehyde, undergoes a1 ,3-dipolar cycloaddition with the NDI acting as dipolarophile forming the intermediate 119 (Scheme 16). As econd 1,3-dipolar cycloaddition takes place affording intermediate 120 with two five-membered rings, whicht hrougharearrangement results in the formation of 121,w ith two six-membered rings as shown in Scheme16.…”

Section: Core Modification Of Ndismentioning

confidence: 99%

Recent Advances in the Core‐Annulation of Naphthalene Diimides

Insuasty

Maniam

Langford

2019

Chemistry A European J

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This review focuses on describing all known synthetic strategies leading to core‐annulation of naphthalene diimides (NDIs). Strategies presented involve the formation of four‐, five‐ and six‐membered ring annulations bearing different heteroatomic and carbocyclic derivatives, including annulenes. The core‐annulation method opens the possibility for obtaining designer molecules with tuneable electronic characteristics such as a reduced energy band gap, and enhanced intermolecular overlap of π‐systems that improve electronic coupling between molecules—which is highly desirable for charge transport properties summarised in the final pages for applications in electronic devices such as organic field‐effect transistors (OFETs) and organic photovoltaic (OPV) cells. Molecular recognition in pH and fluoride sensing, or as a DNA probe, are some of additional applications of core‐annulated NDIs presented here. Additionally, recent advances in core modification of NDIs are presented, opening an entire new chemical avenue to be explored. Finally, the outlook on the future prospect of annulated NDIs in various applications is summarised.

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Unprecedented 1,3-Dipolar Cycloaddition: From 1,4,5,8-Naphthalene Bisimides to a New Heterocyclic Skeleton

Cited by 17 publications

References 29 publications

Strategies for the Synthesis of Functional Naphthalene Diimides

Strategies for the Synthesis of Functional Naphthalene Diimides

Sulfoxide‐Directed Metal‐Free ortho‐Propargylation of Aromatics and Heteroaromatics

Recent Advances in the Core‐Annulation of Naphthalene Diimides

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