Subtle substitution controls the rainbow chromatic behaviour of multi-stimuli responsive core-expanded pyrenes

Hogan, David T.; Gelfand, Benjamin S.; Spasyuk, Denis; Sutherland, Todd C.

doi:10.1039/c9qm00710e

Cited by 26 publications

(25 citation statements)

References 64 publications

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“…PQDC crystallized in the monoclinic space group P 2 1 / c with four molecules per unit cell and one molecule in the asymmetric unit (polymorph α). Recently, the same packing and unit cell have been reported by Sutherland et al . The cyano groups are slightly contorted out of planarity by approximately 2.5°.…”

Section: Resultssupporting

confidence: 75%

“…Despite the attractive low‐lying LUMOs of the few literature‐known cyano PPAs of Scheme , no X‐ray structures giving more detailed information about the above‐mentioned possible arrangement were described to date. The only exception is PQDC , for which a solid‐state structure was described recently . This contribution had a different focus, and therefore no discussion of transfer integrals was done.…”

Section: Introductionmentioning

confidence: 99%

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Di‐ and Tetracyano‐Substituted Pyrene‐Fused Pyrazaacenes: Aggregation in the Solid State

Ueberricke

Ciubotaru

Ghalami

et al. 2020

Chemistry A European J

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Section: Resultssupporting

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Di‐ and Tetracyano‐Substituted Pyrene‐Fused Pyrazaacenes: Aggregation in the Solid State

Ueberricke

Ciubotaru

Ghalami

et al. 2020

Chemistry A European J

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“…By following the general procedure, compound 5q was obtained after purification by column chromatography on silica gel (EtOAc/hexane = 20:80) as a brown solid (56 mg, 62%). 1 H),2 H),8.18 (d,J = 7.1 Hz,1 H),4 H),7.92 (s, 1 H), 7.86 (t, 1 J = 7.7 Hz, 1 H, 2 J = 1.6 Hz), 7.44-7.41 (m, 1 H), 7.10-7.06 (m,2 H),6.84 (d,J = 8.0 Hz,1 H),2 H),2 H). 13 C NMR (~101 MHz, CDCl 3 ):  = 161.9, 150.…”

Section: N-(10-(23-dihydrobenzo[b][14]dioxin-6-yl)pyren-1-yl)picolinamide (5q)mentioning

confidence: 99%

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation and Alkylation of Pyrene Core: Synthesis of C1,C2- and C1,C10-Disubstituted Pyrene Motifs

Dalal

Babu

2021

Synthesis

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We report the application of the Pd(II)-catalyzed, directing group-aided C-H arylation/alkylation tactics to functionalize pyrene core, especially, the relatively inaccessible C2 and K-region C10 positions of pyrene core and augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene motifs. The Pd(II)-catalyzed β-C-H arylation/alkylation of the C2-position of pyrene-1-carboxamide possessing 8-aminoquinoline directing group yielded various C1,C2-disubstituted pyrenes. Similarly, the Pd(II)-catalyzed selective γ-C-H arylation/alkylation of the C10-position of N-(pyren-1-yl)picolinamide possessing picolinamide directing group yielded various C1,C10-disubstituted pyrenes. Examples of C(9)-H arylation of pyrene-1-carboxamide and the removal of the directing group after the C-H arylation/alkylation reactions were also shown. The structures of representative pyrene derivatives were confirmed by the X-ray structure analysis. Given the importance of the pyrene derivatives in various fields of chemical sciences, this report is a contribution towards augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene amide motifs.

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“…Figure 4 D displays a sharp peak which is obtained for the oxygen XPS spectrum at 527.2 eV. Figure 4 E displays a broad peak attained for the carbon XPS spectrum at 285.1 eV 42 . Thus, the XPS analysis demonstrates the successful formation of bimetallic NiFe conjugation with f-MWCNT is zero valent with the presence of C, Ni, and Fe.…”

Section: Resultsmentioning

confidence: 90%

“…Figure 4D displays a sharp peak which is obtained for the oxygen XPS spectrum at 527.2 eV. Figure 4E displays a broad peak attained for the carbon XPS spectrum at 285.1 eV 42 . Thus, the XPS analysis electrocatalytic analysis of nft on nife/f-MWCNT modified hybrid electrode.…”

Section: Resultsmentioning

confidence: 91%

Nano assembly of NiFe spheres anchored on f-MWCNT for electrocatalytic reduction and sensing of nitrofurantoin in biological samples

Hwa

Sharma

2020

Sci Rep

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The current study reports a facile simple, low-cost electrochemical sensor in the detection of nitrofurantoin (nft) by using nife/f-MWcnt hybrid composite as a promising electrocatalyst. nft is an antibiotic drug that is extensively using in pharmaceuticals and also in animal food production which causes a severe threat for both human and animal environments. extending the residues of NFT are left into rivers, soils, lakes, and groundwaters either found or discharged leading health issues. to this nife/f-MWcnt composite was synthesized using a hydrothermal mechanism and then ultrasonicated to form a hybrid composite for catalytic evaluation and electrochemical detection of NFT for the very first time. Furthermore, the physicochemical properties of NiFe nanospheres conjugated on f-MWcnt are scrutinized using various analytical and spectroscopical techniques. Resulting transmission electron microscopy (TEM) displays a chain like NiFe nanospheres anchored on f-MWCNT with a well-defined spherical shape, without any comprehensive agglomeration. The NiFe/f-MWcnt screen printed carbon paste electrode (Spce) displayed an excellent electrocatalytic activity for NFT with a LOD of 0.03 µM and a sensitivity of 11.45 µA µM −1 cm −2. establishing a new selectivity and with the existence of co-interfering compounds. to enhance the practical abilities analysis were performed in Human serum and urine samples which resulted in satisfactory recoveries with high precision and linear accuracy illustrated in Scheme 1. Nitrofurantoin [(NFT)-N-(5-nitro-2-furfurylidene)-1-aminohydantoin], a well-known antimicrobial drug that has shown to actively inhibit several gram-positive as well as gram-negative microbes which belong to the family of nitrofuran 1,2. This drug also has great importance in veterinary medicine in the prevention and treatment of coccidiosis that occurs in poultry and livestock 3,4. It has also been associated with patients of neuropathy, hepatitis, pulmonary fibrosis, and hemolytic anemia suffering from the deficiency of glucose-6-phosphate 5. Despite having such excellent antimicrobial activity, NFT showed some amount of metabolic toxicity 6. The antimicrobial activity of NFT might owe to the fact that 5-nitro function undergoes reductive metabolic activation to form hydroxylamine derivatives, nitroso derivatives, and anion radical which includes a reduction mechanism of the nitro group (-NO 2) 7,8. Basically, the nitrofuran family consists of furaltadone, furazolidone, difurazone, nifurtoniol, nitrofurazone, nifuroxazide, and nitrofurantoin. Conspicuously, within a single daily oral dose usage, NFT gets partially metabolized where 25-50% is excreted as its original state with 1-2% excretes through urine in the form of aminofurantoin 9. NFT also has the versatile ability in generating reactive species of oxygen and NO through its nitro group reduction. Where, by all these factors NFT is vividly released into environmental habitats making the contamination in the ecosystem, even at a quite low amount of level it is harm...

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Subtle substitution controls the rainbow chromatic behaviour of multi-stimuli responsive core-expanded pyrenes

Abstract: Core-expanded pyrenes exhibit rainbow solvatochromism, reversible acidochromism in both solution and solid-state, and reversible crystal-to-crystal mechanochromism all governed by substitution pattern.

Cited by 26 publications

References 64 publications

Di‐ and Tetracyano‐Substituted Pyrene‐Fused Pyrazaacenes: Aggregation in the Solid State

Di‐ and Tetracyano‐Substituted Pyrene‐Fused Pyrazaacenes: Aggregation in the Solid State

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation and Alkylation of Pyrene Core: Synthesis of C1,C2- and C1,C10-Disubstituted Pyrene Motifs

Nano assembly of NiFe spheres anchored on f-MWCNT for electrocatalytic reduction and sensing of nitrofurantoin in biological samples

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