M.W=400-450 | Heterocyclic Building Blocks-Naphthyridine

Han, Yi’s team published research in Angewandte Chemie, International Edition in 59 | CAS: 152873-79-5

Angewandte Chemie, International Edition published new progress about 152873-79-5. 152873-79-5 belongs to naphthyridine, auxiliary class Trifluoromethyl,Sulfonate,Benzene, name is 1,5-NAphthalenebis(trifluoromethanesulfonate), and the molecular formula is C12H6F6O6S2, Synthetic Route of 152873-79-5.

Han, Yi published the artcileFormation of Azulene-Embedded Nanographene: Naphthalene to Azulene Rearrangement During the Scholl Reaction, Synthetic Route of 152873-79-5, the publication is Angewandte Chemie, International Edition (2020), 59(23), 9026-9031, database is CAplus and MEDLINE.

Incorporation of a non-hexagonal ring into a nanographene framework can lead to new electronic properties. During the attempted synthesis of naphthalene-bridged double [6]helicene and heptagon-containing nanographene by the Scholl reaction, an unexpected azulene-embedded nanographene and its triflyloxylated product were obtained, as confirmed by X-ray crystallog. anal. and 2D NMR spectroscopy. A 5/7/7/5 ring-fused substructure containing two formal azulene units is formed, but only one of them shows an azulene-like electronic structure. The formation of this unique structure is explained by arenium ion mediated 1,2-Ph migration and a naphthalene to azulene rearrangement reaction according to an in-silico study. This report represents the first exptl. example of the thermodynamically unfavorable naphthalene to azulene rearrangement and may lead to new azulene-based mol. materials.

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

Takeuchi, Motoharu’s team published research in Journal of Organic Chemistry in 58 | CAS: 152873-79-5

Journal of Organic Chemistry published new progress about 152873-79-5. 152873-79-5 belongs to naphthyridine, auxiliary class Trifluoromethyl,Sulfonate,Benzene, name is 1,5-NAphthalenebis(trifluoromethanesulfonate), and the molecular formula is C38H74Cl2N2O4, Computed Properties of 152873-79-5.

Takeuchi, Motoharu published the artcile[2.2]Naphthalenophanes from intermolecular [2 + 2] photocycloadditions of divinylnaphthalenes, Computed Properties of 152873-79-5, the publication is Journal of Organic Chemistry (1993), 58(26), 7388-92, database is CAplus.

Syn-[2.2]naphthalenophanes, e.g., I, were obtained exclusively in reasonable yields from the intermol. [2 + 2] photocycloadditions of divinylnaphthalenes. The position of the vinyl group and the type of vinyl substituent affected the isomer ratio of the products. The structures of naphthalenophanes were elucidated by ¹H-NMR spectroscopy including COSY and NOESY experiments Among the divinylnaphthalenes examined, 1,4-, 1,5-, and 1,6-ones did not give the desired naphthalenophanes. By taking advantage of the effect of the substituents on the photoreaction, the authors could obtain [2.2](1,5)naphthalenophane derivatives from 1,5-bis(β-carboethoxyethenyl)naphthalene and 1,5-bis(β-phenylethenyl)naphthalene, but the authors could not obtain the 1,4-isomers, probably because they are highly strained. Although a mixture of two different divinylnaphthalenes was irradiated, only homoadducts were obtained; no cross adducts were detected.

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

Barluenga, Jose’s team published research in Angewandte Chemie, International Edition in 45 | CAS: 152873-79-5

Barluenga, Jose published the artcileDirect intramolecular arylation of aldehydes promoted by reaction with IPy₂BF₄/HBF₄: synthesis of benzocyclic ketones, Related Products of naphthyridine, the publication is Angewandte Chemie, International Edition (2006), 45(19), 3140-3143, database is CAplus and MEDLINE.

Aldehydes acylated arenes upon treatment at low temperature with IPy₂BF₄ and HBF₄. This reaction was exploited in a novel intramol. approach to the preparation of benzocyclic ketones, e.g., I. A plausible mechanistic rational was also given.

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

Hindenberg, Philip’s team published research in Angewandte Chemie, International Edition in 60 | CAS: 152873-79-5

Hindenberg, Philip published the artcileEn Route Towards the Control of Luminescent, Optically-Active 3D Architectures, Name: 1,5-NAphthalenebis(trifluoromethanesulfonate), the publication is Angewandte Chemie, International Edition (2021), 60(2), 766-773, database is CAplus and MEDLINE.

π-Extended systems are key components for the development of future organic electronic technologies. While conceiving mols. with improved properties is fundamental for the evolution of materials science, keeping control over the 3D arrangement of mols. represents an ever-expanding challenge. Herein, a synthetic protocol to replace carbon atoms of π-systems by dissym. phosphorus atoms is reported; in particular, it allowed for conceiving new fused phosphapyrene derivatives with improved properties. The presence of dissym. phosphorus atoms precluded the formation of excimers. X-ray diffraction revealed that, meanwhile, strong intermol. interactions are taking place in the solid state. The phosphapyrenes photoluminesce in the visible region with high quantum yields; importantly, they are CD-active. In addition, the unique non-planar features of phosphorus atoms allowed for the control of the 3D arrangement of mols., rendering lemniscate-like structures. Based on our discoveries, we envisage the possibility to construct higher-order, chiral 3D architectures from larger phosphorus-containing π-systems.

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

Berton, Nicolas’s team published research in Chemistry of Materials in 23 | CAS: 152873-79-5

Chemistry of Materials published new progress about 152873-79-5. 152873-79-5 belongs to naphthyridine, auxiliary class Trifluoromethyl,Sulfonate,Benzene, name is 1,5-NAphthalenebis(trifluoromethanesulfonate), and the molecular formula is C12H6F6O6S2, Product Details of C12H6F6O6S2.

Berton, Nicolas published the artcileCopolymer-Controlled Diameter-Selective Dispersion of Semiconducting Single-Walled Carbon Nanotubes, Product Details of C12H6F6O6S2, the publication is Chemistry of Materials (2011), 23(8), 2237-2249, database is CAplus.

The ability of a series of strictly alternating copolymers to selectively enwrap single-walled carbon nanotubes (SWNTs) is studied. Seven copolymers comprising either fluorene or carbazole subunits separated by naphthalene, anthracene, and anthraquinone spacers are obtained in good yields via a Suzuki cross-coupling protocol. The 1,5-linked naphthalene, anthracene, and anthraquinone units are introduced to favor a spiral conformation of the polymer backbone to improve its SWNT wrapping features. Particularly high yields of polymers are obtained using the naphthalene-1,5-ditriflate precursor, highlighting the potential of bifunctional aryltriflates as precursors of copolymers. All polymers disperse HiPco SWNTs in toluene. The obtained dispersions are purified by d. gradient centrifugation and their compositions are analyzed by photoluminescence (PL) spectroscopy. In their dispersing ability the polymers display more or less pronounced SWNT diameter selectivity. In particular, poly(9,9-didodecylfluorene-2,7-diyl-alt-anthracene-1,5-diyl) (P2) exhibits a strong selectivity toward SWNTs having a diameter of 鈮?.95 nm, including close-to-zigzag nanotubes. SWNT dispersions of P2 are further analyzed by absorbance and Raman scattering spectroscopy. The diameter selectivity is attributed to the anthracene-1,5-diyl subunit. In order to combine diameter selectivity with the preference for large chiral angles as shown by polyfluorene, the number of fluorene subunits in the polymer backbone is doubled in P7. Indeed, to some extent, the combination of both selectivities is observed in its dispersing behavior.

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

Vila, Carlos’s team published research in Chemistry – A European Journal in 20 | CAS: 152873-79-5

Chemistry – A European Journal published new progress about 152873-79-5. 152873-79-5 belongs to naphthyridine, auxiliary class Trifluoromethyl,Sulfonate,Benzene, name is 1,5-NAphthalenebis(trifluoromethanesulfonate), and the molecular formula is C25H47NO8, SDS of cas: 152873-79-5.

Vila, Carlos published the artcilePalladium-Catalysed Direct Cross-Coupling of Organolithium Reagents with Aryl and Vinyl Triflates, SDS of cas: 152873-79-5, the publication is Chemistry – A European Journal (2014), 20(41), 13078-13083, database is CAplus and MEDLINE.

A palladium-catalyzed cross-coupling of organolithium reagents with aryl and vinyl triflates is presented. The reaction proceeds at 50 or 70 °C with short reaction times, and the corresponding products are obtained with moderate to high yields, with a variety of alkyl and (hetero)aryl lithium reagents. E.g., in presence of Pd₂(dba)₃ and DavePhos, cross-coupling of butyllithium and 2-naphthyl triflate gave 81% 2-butylnaphthalene.

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

Stevens, Loah A.’s team published research in Chemistry of Materials in 27 | CAS: 152873-79-5

Stevens, Loah A. published the artcileTemperature-Mediated Polymorphism in Molecular Crystals: The Impact on Crystal Packing and Charge Transport, Computed Properties of 152873-79-5, the publication is Chemistry of Materials (2015), 27(1), 112-118, database is CAplus.

The authors report a novel synthesis to ultra high purity 7,14-bis((trimethylsilyl)ethynyl)dibenzo[b,def]chrysene (TMS-DBC) and the use of this material in the growth of single crystals by solution and vapor deposition techniques. The substrate temperature has a dramatic impact on the crystal growth, producing two distinct polymorphs of TMS-DBC; low temperature (LT) fine red needles and high temperature (HT) large yellow platelets. Single crystal x-ray crystallog. confirms packing structures where the LT crystals form a 1-dimensional slipped-stack structure, while the HT crystals adopt a 2-dimensional brickwork motif. Crystallog. data are given. These polymorphs also represent a rare example where both are extremely stable and do not interconvert to the other crystal structure upon solvent or thermal annealing. Single crystal organic field-effect transistors of the LT and HT crystals show that the HT 2-dimensional brickwork motif produces hole mobilities â?.1 cm² V^-1 s^-1, while the mobility of the 1-dimensional structure is significantly lower, at 0.028 cm² V^-1 s^-1. Electronic-structure calculations indicate that the superior charge transport in the brickwork polymorph in comparison to the slipped-stack polymorph is due to the presence of an increased dimensionality of the charge migration pathways.

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

Takahashi, Ikko’s team published research in Chemistry Letters in 46 | CAS: 152873-79-5

Chemistry Letters published new progress about 152873-79-5. 152873-79-5 belongs to naphthyridine, auxiliary class Trifluoromethyl,Sulfonate,Benzene, name is 1,5-NAphthalenebis(trifluoromethanesulfonate), and the molecular formula is C12H9NO, Quality Control of 152873-79-5.

Takahashi, Ikko published the artcileBronsted acid-catalyzed tandem cycloaromatization of naphthalene-based bisacetals: selective synthesis of ortho-fused six-hexagon benzenoids, Quality Control of 152873-79-5, the publication is Chemistry Letters (2017), 46(3), 392-394, database is CAplus.

Naphthalenes bearing two acetal moieties connected by a methylene-2,1-phenylene group underwent regioselective tandem cycloaromatization using a catalytic amount of trifluoromethanesulfonic acid in 1,1,1,3,3,3-hexafluoropropan-2-ol. Five substrates were successfully employed in this protocol to afford ortho-fused six-hexagon benzenoids with high selectivities and in excellent yields.

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

Rao, M. Rajeswara’s team published research in Chemistry – A European Journal in 21 | CAS: 152873-79-5

Rao, M. Rajeswara published the artcileπ-Extended Indenofluorenes, Application In Synthesis of 152873-79-5, the publication is Chemistry – A European Journal (2015), 21(16), 6193-6201, database is CAplus and MEDLINE.

A series of π-extended aromatic indenofluorene (IF) analogs with naphthalene and anthracene cores were synthesized through acid-catalyzed intramol. cyclization. The regioselectivity of the reaction is controlled by a combination of steric and electronic factors and in some cases several possible regioisomers have resulted from the same precursor. The effects of ring connectivity on the optoelectronic properties were studied by DFT calculations, absorption/emission spectroscopy, cyclic voltammetry, and spectroelectrochem. studies. All regioisomers exhibited a red shift of their absorption/emission bands relative to the parent IF analogs, but the magnitude of this shift and other optoelectronic properties (luminescence quantum yield, etc.) depends on the ring connectivity in a less obvious manner.

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

Boominathan, Siva Senthil Kumar’s team published research in Chemistry – A European Journal in 25 | CAS: 152873-79-5

Boominathan, Siva Senthil Kumar published the artcileDiindeno-Fused Dibenzo[a,h]anthracene and Dibenzo[c,l]chrysene: Syntheses, Structural Analyses, and Properties, Related Products of naphthyridine, the publication is Chemistry – A European Journal (2019), 25(30), 7280-7284, database is CAplus and MEDLINE.

Diindeno-fused dibenzo[a,h]anthracene 6 and diindeno-fused dibenzo[c,l]chrysene 9 contain the key moieties 1,4-quinodipropene (1,4-QDP) and 2,6-naphthoquinodipropene (2,6-NQDP), resp., and they both have an open-shell singlet ground state. The latter compound exhibits a strong biradical character and interesting properties, including a low ΔE_T-S (2.44 kcal mol^-1), a small HOMO-LUMO gap (1.06 eV), a wide photoabsorption range (250-1172 nm), and a large two-photon absorption cross-section (σ=1342±56 GM). This work verifies that 6 has a slightly larger HOMO-LUMO gap and ΔE_T-S than its helical isomer diindeno[2,1-f:1′,2′-j]picene (DIP), but is a much stronger two-photon absorber, verifying the important effect of geometry on the photophys. properties.

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