Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes

Zhang, Xinfu; Yu, Haibo; Xiao, Yi

doi:10.1021/jo201413b

Cited by 137 publications

(78 citation statements)

References 23 publications

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“…8,9 Under the same reaction conditions of NH 4 OAc/BuOH at reflux, the yields for di-and tetra-thiophene substituted 3e and 3f were low for both routes but marginally higher when 1f was used as starting substrate (Scheme 5). The use of 2b as starting substrate suffers from the added disadvantage that KCN is required for its synthesis from the precursor chalcone.…”

Section: 4mentioning

confidence: 99%

“…In this approach in situ chelation is performed following the formation of the azadipyrromethene without prior purification. This method has been reported for some tetraaryl 3 9 The first example of a PO 2 chelate phosphorusdioxideazadipyrromethene 38 was synthesized by reaction of azadipyrromethene 3a with POCl 3 in the presence of Et 3 N, followed by aqueous hydrolysis (Scheme 16). 29 This sole example illustrates that the synthesis (and properties) of a broad range of other nonmetal and metalloid chelates remains to be explored.…”

Section: Scheme 13 Synthesis Of Bf2-azadipyrromethenementioning

confidence: 99%

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Azadipyrromethenes: from traditional dye chemistry to leading edge applications

2016

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Azadipyrromethenes were first described over 70 years ago as blue pigments, but now are rapidly emerging as a compound class with highly desirable near infrared photophysical properties. Since the turn of the century several routes to azadipyrromethenes have been developed and numerous post-synthesis derivatizations have allowed for their exploitation in both biological and material sciences. The relative ease of access to specifically designed derivatives is now allowing their use in multiple technological formats from real-time fluorescence imaging, to solar energy materials, to optoelectronic devices and many more. In this review we have highlighted the synthetic component of this story as it is the ability to generate the designer azadipyrromethene that opens the door to exciting applications.

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Section: 4mentioning

confidence: 99%

Section: Scheme 13 Synthesis Of Bf2-azadipyrromethenementioning

confidence: 99%

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

2016

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“…26,27 Enhancement of co-planarity between phenyls and the central core results in NIR bathochromic shifts, probably due to electron delocalization. 28 Diphenyl dithienyl aza-BODIPY was synthesized through the substitution of phenyl groups by thiophene in aza-BODIPY. Remarkable red shifts and strong NIR fluorescence could be found.…”

Section: Bodipy-based Nirf Probesmentioning

confidence: 99%

“…Remarkable red shifts and strong NIR fluorescence could be found. 28 Bromo-substituted BODIPY containing thienopyrrole moieties was reported by Yang's group. Exposure of these products in the NIR region exhibited a high singlet oxygen quantum yield that leads to photo cytotoxicity.…”

Section: Bodipy-based Nirf Probesmentioning

confidence: 99%

Near-infrared fluorescent probes in cancer imaging and therapy: an emerging field

Yi¹,

Wang²,

Qin³

et al. 2014

IJN

211

149

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Near-infrared fluorescence (NIRF) imaging is an attractive modality for early cancer detection with high sensitivity and multi-detection capability. Due to convenient modification by conjugating with moieties of interests, NIRF probes are ideal candidates for cancer targeted imaging. Additionally, the combinatory application of NIRF imaging and other imaging modalities that can delineate anatomical structures extends fluorometric determination of biomedical information. Moreover, nanoparticles loaded with NIRF dyes and anticancer agents contribute to the synergistic management of cancer, which integrates the advantage of imaging and therapeutic functions to achieve the ultimate goal of simultaneous diagnosis and treatment. Appropriate probe design with targeting moieties can retain the original properties of NIRF and pharmacokinetics. In recent years, great efforts have been made to develop new NIRF probes with better photostability and strong fluorescence emission, leading to the discovery of numerous novel NIRF probes with fine photophysical properties. Some of these probes exhibit tumoricidal activities upon light radiation, which holds great promise in photothermal therapy, photodynamic therapy, and photoimmunotherapy. This review aims to provide a timely and concise update on emerging NIRF dyes and multifunctional agents. Their potential uses as agents for cancer specific imaging, lymph node mapping, and therapeutics are included. Recent advances of NIRF dyes in clinical use are also summarized.

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“…[33][34][35] Recently, the complicated synthetic mechanism of aza-BODIPY has been unveiled, 36,37 allowing for further development of new aza-BODIPY analogues. 38,39 In addition, a chemical modification of the aza-BODIPY core similar to BODIPYs, as described below, basically contributes to a red shift of the fluorescence emission. 2·2·2 "Coupled" BODIPY (36 -79, Fig.…”

Section: ·2 Nir Emitting Bodipys By Chemical Modification 2·2·1 Aza-mentioning

confidence: 99%

New Trends in Near-Infrared Fluorophores for Bioimaging

2014

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Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes

Abstract: In the orignial 1,3,5,7-tetraphenyl aza-BODIPY, replacing the phenyl rings with thiophene achieved significant bathochromic shifts. One of the target molecules, DPDTAB, emitting strong NIR fluorescence with a quantum yield of 0.46 in acetonitrile, is a very competitive NIR fluorophore.

Cited by 137 publications

References 23 publications

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

Azadipyrromethenes: from traditional dye chemistry to leading edge applications

Near-infrared fluorescent probes in cancer imaging and therapy: an emerging field

New Trends in Near-Infrared Fluorophores for Bioimaging

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