Heterocyclic Building Blocks-Naphthyridine

Bhanuchandra, M. published the artcileSynthesis of Spirocyclic Diarylfluorenes by One-Pot Twofold S_NAr Reactions of Diaryl Sulfones with Diarylmethanes, Category: naphthyridine, the publication is Organic Letters (2016), 18(3), 384-387, database is CAplus and MEDLINE.

Treatment of dibenzothiophene dioxides I (R¹ = R² = H; R¹ = 2-Ph, R² = H, 9-Ph; R¹ = 3-Cl, R² = 7-Cl; etc.) with cyclic diarylmethanes II (X = nothing, CH₂, CMe₂, O, S, R³ = H; X = S, R³ = OH, MeO, CF₃, Ph, etc.) in the presence of KN(SiMe₃)₂ resulted in the formation of fluorene-based spirocyclic tetraarylmethanes III in a single operation. The transformation proceeds via an intermol. S_NAr reaction of the dioxides with cyclic diarylmethylpotassium followed by intramol. S_NAr cyclization. This straightforward strategy provides a wide range of spirocyclic diarylfluorenes including unusual ones that are otherwise difficult to synthesize.

Organic Letters published new progress about 159-62-6. 159-62-6 belongs to naphthyridine, auxiliary class Other Aromatic Heterocyclic,Spiro, name is Spiro[fluorene-9,9′-xanthene], and the molecular formula is C25H16O, Category: naphthyridine.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Yang, Lei published the artcileTheoretical Studies on Novel Gridspiroarenes: Structures, Noncovalent Interactions and Reorganization Energies, Related Products of naphthyridine, the publication is Chinese Journal of Chemistry (2019), 37(9), 915-921, database is CAplus.

Organic semiconductor materials with low reorganization energy have various applications such as in organic light-emitting diodes (OLEDs), organic field-effect transistor (OFETs) and organic solar cells (OSCs). In this work, we have designed a new class of gridspiroarenes (GS-SFX and GS-SITF) with #-shaped structures, which have novel crisscross geometrical structures compared to widely used spirocyclic arenes-SFX and SITF. The structure electronic properties, adiabatic ionization potentials (IP_a), adiabatic electron affinities (EA_a) and reorganization energies (λ) of GS-SFX and GS-SITF have been calculated using d. functional theory (DFT) method. The calculated HOMO and LUMO spatial distributions suggest that GS-SFX and GS-SITF have better transport properties. The noncovalent interaction anal. shows the weak intramol. interactions between their arms. The results indicate that the reorganization energies of GS-SFX and GS-SITF are significantly reduced compared to the dimer structures-DSFX and DSITF. Furthermore, the GS-SITF1 which is one of the isomers of GS-SITF exhibits the lowest values for λ(h) (0.067 eV) and λ(e) (0.153 eV). Therefore, we believe the predicted structure, electronic property, and reorganization energy are good indicator for transport materials. This work has systematically studied the effect of gridization, which provides insights to design organic semiconductor materials with excellent charge transport properties.

Chinese Journal of Chemistry published new progress about 159-62-6. 159-62-6 belongs to naphthyridine, auxiliary class Other Aromatic Heterocyclic,Spiro, name is Spiro[fluorene-9,9′-xanthene], and the molecular formula is C23H28N2O4, Related Products of naphthyridine.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Yu, Hui published the artcileEvaluation of “Click” Binaphthyl Chiral Stationary Phases by Liquid Chromatography, Application In Synthesis of 2960-93-2, the publication is Chirality (2012), 24(5), 391-399, database is CAplus and MEDLINE.

Two click binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatog. Their structures incorporate S-(-)-1,1′-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of racemic BINOL derivatives, particularly for nonpolar diether derivatives and 3-Ph indolin-2-one analogs. The chromatog. data showed that the π-π interaction was crucial for enantiorecognition of these CSPs. Loss of enantioselectivity observed on CSP3, which are lacking the triazole ring linkage, indicated that the triazole ring linkage took part in the enantioseparation process, although it was remote from the chiral selector of the CSP. The substitution of the Ph group at 6 and 6′ positions can significantly improve the separation ability of the CSP. The chiral recognition mechanism was also studied by tracking the elution orders and studying the thermodn. parameters. Chirality 00:000-000, 2012. Copyright © 2012 Wiley Periodicals, Inc.

Chirality published new progress about 2960-93-2. 2960-93-2 belongs to naphthyridine, auxiliary class Naphthalene,Ether,Other MOF ligands,Organic ligands for MOF materials, name is 2,2′-Dimethoxy-1,1′-binaphthalene, and the molecular formula is C16H12O, Application In Synthesis of 2960-93-2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Tabanligil Calam, Tugba published the artcileElectrochemical determination of 8-hydroxyquinoline in a cosmetic product on a glassy carbon electrode modified with 1-amino-2-naphthol-4-sulphonic acid, Computed Properties of 116-63-2, the publication is Instrumentation Science & Technology (2021), 49(1), 1-20, database is CAplus.

A new voltammetric method was developed for the simple, rapid and inexpensive determination of 8-hydroxyquinoline (8HQ) on a modified electrode obtained by the electrodeposition of 1-amino-2-naphthol-4-sulfonic acid (ANSA) on the surface of a glassy carbon (GC) electrode. The electrode interfacial properties were investigated by electrochem. impedance spectroscopy (EIS). The electrochem. response of the ANSA-GC electrode toward 8-hydroxyquinoline was investigated by the use of square wave voltammetry. The ANSA-GC modified electrode showed two linear plots with 8-hydroxyquinoline concentrations from 5 x 10^-7 to 1.4 x 10^-5 mol dm^-3 (R² of 0.9984) and from 1.4 x 10^-5 to 4.25 x 10^-4 mol dm^-3 with a correlation coefficient R² equal to 0.9967. The limit of detection was 1.6 x 10^-7 mol dm^-3. The ANSA-GC modified electrode also showed excellent stability and reproducibility for up to two weeks. The anal. application of the ANSA-GC modified electrode was investigated for the determination of 8-hydroxyquinoline in a blush cosmetic product. The results in good agreement to those obtained by spectrophotometry as a standard method.

Instrumentation Science & Technology published new progress about 116-63-2. 116-63-2 belongs to naphthyridine, auxiliary class Sulfonic acid,Amine,Naphthalene,Alcohol,Organic Pigment, name is 4-Amino-3-hydroxynaphthalene-1-sulfonic acid, and the molecular formula is C24H20Ge, Computed Properties of 116-63-2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Fun, Hoong Kun published the artcile2,7-Dimethyl-1,8-naphthyridine, Computed Properties of 14903-78-7, the publication is Acta Crystallographica, Section E: Structure Reports Online (2009), 65(8), o1747, database is CAplus and MEDLINE.

The asym. unit of 2,7-di-Me-1,8-naphthyridine, C₁₀H₁₀N₂, contains 1/2-mol. with the 2 shared C atoms lying on a 2-fold rotation axis. The 1,8-naphthyridine is almost planar with a dihedral angle of 0.42(3)° between the fused pyridine rings. In the crystal, mols. are linked into infinite chains along the c axis by intermol. C-H···N H bonds, generating R₂²(8) ring motifs. The crystal structure is further stabilized by C-H···π interactions. Crystallog. data are given.

Acta Crystallographica, Section E: Structure Reports Online published new progress about 14903-78-7. 14903-78-7 belongs to naphthyridine, auxiliary class 6.6_Aromatics,Naphthyridines, name is 2,7-Dimethyl-1,8-naphthyridine, and the molecular formula is C10H10N2, Computed Properties of 14903-78-7.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Dai, Zhi published the artcileSolution-phase synthesis and evaluation of tetraproline chiral stationary phases, Application of 2,2′-Dimethoxy-1,1′-binaphthalene, the publication is Chirality (2012), 24(4), 329-338, database is CAplus and MEDLINE.

Fmoc-Pro-Pro-Pro-Pro-OH and Fmoc-Pro-Pro-Pro-Pro-NMe(CH₂)₃CO₂H were prepared on multigramm scale by a solution-phase synthetic route; the two peptides were attached to (methylamino)propylated silica gel, deprotected, and acylated with pivaloyl chloride to provide silica gel-bound Me₃CCO-Pro-Pro-Pro-Pro-N(Me)CH₂CH₂CH₂R (R = silica) and Me₃CCO-Pro-Pro-Pro-Pro-NMe(CH₂)₃CONHCH₂CH₂CH₂R (R = silica) as chiral stationary phases for the separation of a variety of organic analytes. The resolution of analytes with the two chiral stationary phases prepared from tetraproline peptides were compared to the resolution of analytes by tetraproline synthesized on (methylamino)propylated silica gel; all three silica-bound tetraproline peptides had similar chromatog. performance for resolving the 53 model analytes tested. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. © 2012 Wiley Periodicals, Inc.

Chirality published new progress about 2960-93-2. 2960-93-2 belongs to naphthyridine, auxiliary class Naphthalene,Ether,Other MOF ligands,Organic ligands for MOF materials, name is 2,2′-Dimethoxy-1,1′-binaphthalene, and the molecular formula is C22H18O2, Application of 2,2′-Dimethoxy-1,1′-binaphthalene.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Liu, Kuan published the artcileSpiro[fluorene-9,9′-xanthene]-based hole transporting materials for efficient perovskite solar cells with enhanced stability, HPLC of Formula: 159-62-6, the publication is Materials Chemistry Frontiers (2017), 1(1), 100-110, database is CAplus.

Four spiro[fluorene-9,9′-xanthene] (SFX)-based hole transporting materials (HTMs) functionalized with four-armed arylamine moieties located at different positions are designed and synthesized. These compounds exhibit HOMO (HOMO) energy levels of -4.9 to -5.1 eV and a hole mobility of 2.2 to 15 × 10^-5 cm² V^-1 s^-1 after doping. Perovskite solar cells (PSCs) based on a methylammonium lead iodide (MAPbI₃) active layer using one of these HTMs (mp-SFX-2PA) exhibit power conversion efficiencies (PCEs) of up to 16.8%, which is higher than that of the control devices based on benchmark spiro-OMeTAD under the same conditions (15.5%). PSCs based on mp-SFX-2PA exhibit better stability (retain 90% of their initial PCEs after 2000 h storage in an ambient atm.) than the control devices based on spiro-OMeTAD (retain only 28% of their initial PCEs). mp-SFX-2PA based devices employing a mixed formamidinium lead iodide (FAPbI₃)/methylammonium lead bromine (MAPbBr₃) perovskite layer exhibit an improved PCE of 17.7%. The effects of arylamines and their location positions on device performance are discussed.

Materials Chemistry Frontiers published new progress about 159-62-6. 159-62-6 belongs to naphthyridine, auxiliary class Other Aromatic Heterocyclic,Spiro, name is Spiro[fluorene-9,9′-xanthene], and the molecular formula is C25H16O, HPLC of Formula: 159-62-6.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Govindan, Venkatesan published the artcileLow-cost synthesis of heterocyclic spiro-type hole transporting materials for perovskite solar cell applications, Safety of Spiro[fluorene-9,9′-xanthene], the publication is New Journal of Chemistry (2018), 42(9), 7332-7339, database is CAplus.

Four heterocyclic spiro-type hole transporting materials (HTMs) carrying a spiro[fluorene-9,9′-xanthene] (SFX) (SFX-TPAM and SFX-TPA) or spiro[fluorene-9,9′-thioxanthene] (SFT) unit (SFT-TPAM and SFT-TPA) were synthesized through a low-cost facile route with high yields for perovskite solar cell (PSC) applications. In terms of absorption, these four compounds in the film state are all transparent at wavelengths longer than 430 nm, which is beneficial for allowing visible light to reach the perovskite active layer without being absorbed by the hole transporting layer (HTL). The photovoltaic performance of the inverted PSCs based on these small mol. HTMs with the device architecture of glass/ITO/HTL/CH₃NH₃PbI₃/C₆₀/BCP/Ag was tested. Only SFX-TPAM had its HOMO (HOMO) level matched with the valence band of CH₃NH₃PbI₃. The inverted PSC based on a dopant-free SFX-TPAM HTL achieves a power conversion efficiency of 10.23% under the illumination of standard one sun lighting, which is better than that (8.17%) of the cell based on dopant-free spiro-OMeTAD. The better photovoltaic performance of SFX-TPAM compared to spiro-OMeTAD may be due to the MAPbI₃ film deposited on it having better quality. These results indicate that the facilely synthesized, low-cost SFX based small mols. can be used as the HTMs for PSCs.

New Journal of Chemistry published new progress about 159-62-6. 159-62-6 belongs to naphthyridine, auxiliary class Other Aromatic Heterocyclic,Spiro, name is Spiro[fluorene-9,9′-xanthene], and the molecular formula is C25H16O, Safety of Spiro[fluorene-9,9′-xanthene].

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Kim, Ju-Young published the artcileActivation of Protein Kinase G (PKG) Reduces Neointimal Hyperplasia, Inhibits Platelet Aggregation, and Facilitates Re-endothelialization, Related Products of naphthyridine, the publication is Scientific Reports (2016), 36979, database is CAplus and MEDLINE.

In spite of its great success in reducing restenosis, drug-eluting stent (DES) has unfavorable aspects such as stent thrombosis and delayed re-endothelialization. We examined the effects of PKG activation by Exisulind on neointimal formation, platelet aggregation, and re-endothelialization. Exisulind significantly reduced VSMCs viability, cell cycle progression, migration, and neointimal hyperplasia after vascular injury in rat carotid arteries. Interestingly, in contrast to the effect on VSMC viability, Exisulind did not reduce the viability of endothelial cells. Increased PKG activity by Exisulind inhibited PDGF-stimulated phenotype change of VSMCs from a contractile to a synthetic form. Conversely, the use of PKG inhibitor or gene transfer of dominant-neg. PKG reversed the effects of Exisulind, resulting in the increased viability of VSMCs and neointimal formation. In addition, Exisulind facilitated the differentiation of peripheral blood mononuclear cells to endothelial lineage via PKG pathway, while inhibiting to VSMCs lineage, which was correlated with the enhanced re-endothelialization in vivo. Finally, Exisulind reduced platelet aggregation, which was mediated via PKG activation. This study demonstrated that Exisulind inhibits neointimal formation and platelet aggregation while increasing re-endothelialization via PKG pathway. These findings suggest that Exisulind could be a promising candidate drug of DES for the prevention of restenosis without other complications.

Scientific Reports published new progress about 59973-80-7. 59973-80-7 belongs to naphthyridine, auxiliary class Immunology/Inflammation,COX, name is Sulindac sulfone, and the molecular formula is C20H17FO4S, Related Products of naphthyridine.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem

Lee, Yong-Kyung published the artcileSynthesis of novel chiral poly(methacrylate)s bearing urethane and cinchona alkaloid moieties in side chain and their chiral recognition abilities, Product Details of C22H18O2, the publication is Polymer (2002), 43(26), 7539-7547, database is CAplus.

Two types of new chiral methacrylates, cinchoninyl(2-methacryloyloxyethyl)carbamate (CIMOC) and cinchonidinyl(2-methacryloyloxy-ethyl)carbamate (CDMOC) were synthesized from 2-methacryloyloxyethyl isocyanate (MOI) and cinchona alkaloid such as cinchonine and cinchonidine, resp. Radical polymerizations of CIMOC and CDMOC were performed under several conditions to obtain the corresponding polymers whose specific optical rotations ([α]₄₃₅²⁵) were 84.0-89.0° and 0.39-0.72°, resp. From the results of radical copolymerizations of RMOC (CIMOC and CDMOC, M₁) with styrene (ST, M₂) or Me methacrylate (MMA, M₂), monomer reactivity ratios (r₁, r₂) and Alfrey-Price Q-e were determined: r₁ = 0.18, r₂ = 0.48, Q₁ = 0.53, e₁ = 0.92 for the CIMOC-ST system; r₁ = 0.53, r₂ = 0.26, Q₁ = 4.91, e₁ = 1.80 for the CIMOC-MMA system r₁ = 0.59, r₂ = 0.47, Q₁ = 0.86, e₁ = 0.33 for the CDMOC-ST system; r₁ = 0.28, r₂ = 0.59, Q₁ = 2.15, e₁ = 1.74 for the CDMOC-MMA system. The chiroptical properties of the copolymers were strongly influenced by co-units. Poly(RMOC)-bonded-silica gel as chiral stationary phase (CSP) was prepared for HPLC. The CSPs resolved some racemates such as mandelic acid and trans-2-dibenzyl-4,5-di(o-hydroxyphenyl)-1,3-dioxolane by HPLC. The chiral recognition ability of poly(RMOC) may be due to the interaction between some cinchona alkaloid units and the racemates and/or to secondary and higher-ordered structures of the polymer.

Polymer published new progress about 2960-93-2. 2960-93-2 belongs to naphthyridine, auxiliary class Naphthalene,Ether,Other MOF ligands,Organic ligands for MOF materials, name is 2,2′-Dimethoxy-1,1′-binaphthalene, and the molecular formula is C22H18O2, Product Details of C22H18O2.

Referemce:
https://en.wikipedia.org/wiki/1,8-Naphthyridine,
1,8-Naphthyridine | C8H6N2 – PubChem