Discovery of a Full‐Color‐Tunable Fluorescent Core Framework through Direct CH (Hetero)arylation of N‐Heterocycles

Liu, Bo; Zhi, Wei; Wu, Ningjie; Li, Mingliang; You, Jingsong; Lan, Jingbo

doi:10.1002/chem.201103329

Cited by 138 publications

(63 citation statements)

References 63 publications

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“…Among the many established transition‐metal‐catalyzed C−H bond functionalization procedures for biaryl linkages, direct arylation is often the method of choice in the synthesis of functional organic materials . The advantages of fewer synthetic steps, the use of inexpensive and widely accessible aryl halides, and high atom economy has prompted many research groups to use this methodology for the synthesis of color‐tunable libraries of fluorophores based on various heterocyclic skeletons, for example, diketopyrrolopyrroles, indolizines, or 4,4‐difluoro‐4‐bora‐3 a ,4 a ‐diaza‐ s ‐indacenes (BODIPYs) …”

Section: Introductionmentioning

confidence: 99%

Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red‐Emitting Dyes with Conformational Freedom

Sadowski

Rode

Gryko

2017

Chemistry A European J

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A series of bis-aryl dipyrrolonaphthyridinediones (DPNDs) with various substitution patterns have been designed and synthesized by direct arylation. This reaction occurs regioselectively at positions 3 and 9, which gives a straightforward entry to unique dyes that absorb in the red/far-red region and emit in the far-red/NIR region. The photophysical properties (absorption and fluorescence wavelength) can be controlled by altering the steric hindrance and electronic character of the peripheral aryl group. The fluorescence quantum yields are moderate in the majority of cases and almost independent of changes in the solvent polarity. DPNDs bearing substituents at the ortho position that prevent free rotation of the phenyl ring emit stronger fluorescence relative to the unhindered para analogues and, at the same time their absorption and emission bands are blueshifted. We have used computational methods to explain why electron-donating substituents have significantly stronger effects than electron-withdrawing substituents on the optical properties by invoking the electron-accepting character of the DPND. Electrochemical measurements revealed that the HOMO and LUMO, as well as the electrochemical band gap, also depend strongly on the electronic character of the peripheral group.

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Section: Introductionmentioning

confidence: 99%

Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red‐Emitting Dyes with Conformational Freedom

Sadowski

Rode

Gryko

2017

Chemistry A European J

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“…[11,16] Typical synthetic approaches to these products include cyclizations with synthetic pyridine or pyrrole derivatives, [17][18][19] substitution on preformed indolizines, [20] or 1,3-dipolar cycloaddition with pyridinium ylides. [11,16] Typical synthetic approaches to these products include cyclizations with synthetic pyridine or pyrrole derivatives, [17][18][19] substitution on preformed indolizines, [20] or 1,3-dipolar cycloaddition with pyridinium ylides.…”

Section: As Illustrated Inmentioning

confidence: 99%

Development and Cycloaddition Reactivity of a New Class of Pyridine‐Based Mesoionic 1,3‐Dipole

et al. 2016

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We describe here the development and structural characterization of a new type of mesoionic 1,3-dipole, which can be generated in the one-step reaction of imines with pyridine- or quinoline-based acid chlorides. Coupling the formation of these dipoles with alkyne cycloaddition can open a general and modular route to synthesize indolizines from combinations of available and diversifiable building blocks.

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“…In fact, xanthines such as caffeine, theophylline and theobromine, purines, imidazoles, thiazoles, oxazoles, 1,2,3-triazoles, and N-heteroarene N-oxides were efficiently arylated using p-chlorotoluene as a model electrophilic partner (Scheme 14) [26].…”

Section: Direct Arylations Of Heteroarenes With Aryl Chloridesmentioning

confidence: 99%

Recent Developments in Pd-Catalyzed Direct Arylations of Heteroarenes with Aryl Halides

Bellina

2015

C-H Bond Activation and Catalytic Functionalization I

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The direct arylation of heteroaromatic compounds with aryl halides using palladium catalysts has significantly been developed as an effective method for making (hetero)aryl-heteroaryl bonds, which are frequently found in biologically active compounds and functional materials. However, issues regarding costly reagents, regioselectivity, and harsh reaction conditions have to be solved to really compete with the classical transition metal-mediated cross-coupling procedures involving stoichiometric organometallic reagents. In this review, the most relevant developments aimed at solving these issues are summarized

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Discovery of a Full‐Color‐Tunable Fluorescent Core Framework through Direct CH (Hetero)arylation of N‐Heterocycles

Cited by 138 publications

References 63 publications

Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red‐Emitting Dyes with Conformational Freedom

Direct Arylation of Dipyrrolonaphthyridinediones Leads to Red‐Emitting Dyes with Conformational Freedom

Development and Cycloaddition Reactivity of a New Class of Pyridine‐Based Mesoionic 1,3‐Dipole

Recent Developments in Pd-Catalyzed Direct Arylations of Heteroarenes with Aryl Halides

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