Sterically Protected N<sub>2</sub>O-Type Benzopyrromethene Boron Complexes from Boronic Acids with Intense Red/Near-Infrared Fluorescence

Chen, Na; Zhang, Wenjie; Chen, Shun; Wu, Qinghua; Yu, Changjiang; Wei, Yun; Xu, Yuekang; Hao, Erhong; Jiao, Lijuan

doi:10.1021/acs.orglett.7b00601

Cited by 51 publications

(28 citation statements)

References 57 publications

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“…The isomer 21h , an N‐H acid, with ∆ H acid and ∆ G acid values of 251.9 and 244.4 kcal mol −1 is one of the strongest organic acids reported so far. Literature review shows that the boron derivatives of pyrrole are readily synthesized . Hence, synthesis of these organic superacid is recommended.…”

Section: Resultsmentioning

confidence: 99%

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX₂(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Parsazadeh

Valadbeigi

Rouhani

2019

Int J of Quantum Chemistry

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New classes of organic Brønsted acids were designed with pyrrole and cyclopentadiene scaffolds, and their acidity was assessed theoretically by the B3LYP/6‐311++G(d,p) method. The hydrogen atom of NH group in pyrrole was substituted by an –BX2 (X = H, F, Cl, CN, CF3). The boron atom stabilizes the conjugated bases by interaction with the center of negative charge after deprotonation. The acidity of the compounds was promoted by substitution of the hydrogen atoms of the rings with CN moiety as a strong electron withdrawing group. Also, after deprotonation, delocalization of the negative charge in both pyrrole and cyclopentadiene rings causes stability of the conjugated bases and consequently enhances the acidity. The charge delocalization in the neutral acids and their conjugated bases was compared using nucleus‐independent chemical shift index. Enthalpies and Gibbs free energies of deprotonation in gas phase, ∆Hacid and ∆Gacid, were used as a measure of acidity. Both compounds with isolated and fused pyrrole and cyclopentadiene rings were investigated and it was found that the formers are more acidic. Using these strategies, several acids and superacids with wide range of acidity with ∆Gacid values of 244 to 328 kcal mol−1 were obtained.

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Section: Resultsmentioning

confidence: 99%

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX₂(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Parsazadeh

Valadbeigi

Rouhani

2019

Int J of Quantum Chemistry

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“…In PTZ-P4 , a red emitting fluorophore ( BOBPY ) was chosen to conjugate with phenothiazine ethylidene malononitrile. BOBPY and derivatives were first developed by Jiao and coworkers, 23 and they are a kind of N 2 O-type benzopyrromethene boron complex, wherein axial positions are substituted by corresponding boronic acids. We chose BOBPY here because of its excellent stability and high fluorescence quantum yield in different media.…”

Section: Resultsmentioning

confidence: 99%

Reductive cleavage of CC bonds as a new strategy for turn-on dual fluorescence in effective sensing of H₂S

Wang¹,

Cheng²,

Tan³

et al. 2018

Chem. Sci.

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“…The phenanthrene-fused structure of L40BF, L40BPh, L40BNaph, and L40BPyr efficiently shifts the absorption/emission to the longer wavelength region ( abs : 629-647 nm,  em : 649-670 nm) compared to the previously reported nonfused N 2 O BODIPYs. 123,124 Each enantiomer of L40BPh exhibited a Cotton effect in the deep-red region (|Δ| ≈ 23 at 652 nm), and stable with respect to racemization at room temperature.…”

Section: Account Synlettmentioning

confidence: 99%

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Chiba¹,

Nakamura²,

Matsuoka³

et al. 2020

Synlett

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The dipyrrin–metal complexes and especially the boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have recently attracted considerable attention because of their interesting properties and possible applications. We have developed two unique and useful ways to extend versatility and usefulness of the dipyrrin complexes. The first one is the linear and macrocyclic oligomerization of the BODIPY units. These arrangements of the B–F moieties of the oligomerized BODIPY units provide sophisticated functions, such as unique recognition ability toward cationic guest, associated with changes in the photophysical properties by utilizing unprecedented interactions between the B–F and a cationic species. The second one is introduction of additional ligating moieties into the dipyrrin skeleton. The multidentate N2Ox dipyrrin ligands thus obtained form a variety of complexes with 13 and 14 group elements, which are difficult to synthesize using the original N2 dipyrrin derivatives. Interestingly, these unique complexes exhibit novel structures, properties, and functions such as guest recognition, stimuli-responsive structural conversion, switching of the optical properties, excellent stability of the neutral radicals, etc. We believe that these multifunctional dipyrrin complexes will advance the basic chemistry of the dipyrrin complexes and develop their applications in the materials and medicinal chemistry fields.1 Introduction2 Linear Oligomers of Boron–Dipyrrin Complexes3 Cyclic Oligomers of Boron–Dipyrrin Complexes4 A Cyclic Oligomer of Zinc–Dipyrrin Complexes5 Group 13 Element Complexes of N2Ox Dipyrrins6 Chiral N2 and N2Ox Dipyrrin Complexes7 Group 14 Element Complexes of N2O2 Dipyrrins8 Other N2O2 Dipyrrin Complexes with Unique Properties and Functions9 Conclusion

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Sterically Protected N₂O-Type Benzopyrromethene Boron Complexes from Boronic Acids with Intense Red/Near-Infrared Fluorescence

Cited by 51 publications

References 57 publications

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX₂(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX₂(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Reductive cleavage of CC bonds as a new strategy for turn-on dual fluorescence in effective sensing of H₂S

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

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Sterically Protected N2O-Type Benzopyrromethene Boron Complexes from Boronic Acids with Intense Red/Near-Infrared Fluorescence

Cited by 51 publications

References 57 publications

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX2(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX2(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Reductive cleavage of CC bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

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Product

Resources

About

Sterically Protected N₂O-Type Benzopyrromethene Boron Complexes from Boronic Acids with Intense Red/Near-Infrared Fluorescence

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX₂(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Design of new organic superacids with fused and isolated pyrrole and cyclopentadiene rings and assessment of effect of –BX₂(X = H, F, Cl, CN) substituents on the acidity enhancement: A DFT analysis

Reductive cleavage of CC bonds as a new strategy for turn-on dual fluorescence in effective sensing of H₂S