Category: 18512-55-5

Mishiba, Kentaro published the artcileDimesitylborylethynylated Arenes: Unique Electronic and Photophysical Properties Caused by Ethynediyl (CC) Spacers, Application of 9,10-Diethynylanthracene, the publication is Chemistry – A European Journal (2021), 27(17), 5432-5438, database is CAplus and MEDLINE.

Herein, the authors report the synthesis and electrochem. and photophys. properties of aromatic hydrocarbons having one or two dimesitylborylethynyl peripherals. The mono- (1) and diboryl compounds (2), readily prepared by nucleophilic substitution reaction, are fairly stable to air and moisture in the solid state. The inserted ethynediyl (CC) spacer cancels the steric hindrance between the bulky dimesitylboryl groups and aromatic rings, leading to effective π conjugation over the B-CC-Ar linkages, as revealed by cyclic voltammetry. Despite the small structural differences, the photophys. properties of the benzene, naphthalene, and anthracene derivatives are different. Virtually no emission was observed from the benzene derivatives, whereas the anthracene derivatives emitted with high quantum yields both in solution and in the solid state. Notably, the naphthalene derivatives showed aggregation-induced emission behavior. Unlike the common sterically congested triarylborane derivatives reported so far, the anthracene derivatives showed π-π^*-type absorption and emission bands, which derive from efficient intramol. orbital interactions between the B centers and anthracene moieties, as supported by DFT calculations As a result, the dimesitylborylethynyl substituents effectively lower the LUMO levels of the aromatic hydrocarbon parts, whereas the HOMO levels are almost unaffected, thereby leading to materials with controllable HOMO-LUMO gaps.

Chemistry – A European Journal published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Application of 9,10-Diethynylanthracene.

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

Grisorio, Roberto published the artcileAll-donor poly(arylene-ethynylene)s containing anthracene and silole-based units: Synthesis, electronic and photovoltaic properties, Recommanded Product: 9,10-Diethynylanthracene, the publication is Journal of Polymer Science, Part A: Polymer Chemistry (2013), 51(22), 4860-4872, database is CAplus.

The manuscript deals with the synthesis and properties of four new all-donor alternating poly(arylene-ethynylene)s DBSA, DBSTA, DTSA, and DTSTA. The polymers have been obtained by a Sonogashira cross-coupling of 9,10-diethynyl-anthracene with the dibromo-derivatives of 9,9-dioctyl-dibenzosilole (DBSA), 2,7-dithienyl-9,9-dioctyl-dibenzosilole (DBSTA), 4,4-dioctyl-dithienosilole (DTSA), or 2,6-dithienyl-9,9-dioctyl-dithienosilole (DTSTA). The polymers exhibited absorption profiles and frontier orbital energies strongly dependent on their primary structure. D. functional theory calculations confirmed exptl. observations and provided an insight into the electronic structure of the macromols. In particular, the effects exerted by the thiophene units in DBSTA and DTSTA on the optical properties of the corresponding polymers could be rationalized with respect to DBSA and DTSA. Preliminary photovoltaic measurements have established that the performance of DTSA is among the highest reported for an all-donor polymer. Moreover, UV irradiation of DTSA films under air evidenced a remarkable photostability of this material, providing further evidence that ethynylene-containing electron-rich systems are promising donors for organic solar cells applications. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013.

Journal of Polymer Science, Part A: Polymer Chemistry published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Recommanded Product: 9,10-Diethynylanthracene.

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

Lee, Dae Hee published the artcileHigh-performance low-bandgap conjugated polymers bearing diethynylanthracene units for thin-film transistors, Category: naphthyridine, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(37), 3896-3898, database is CAplus and MEDLINE.

Novel donor-acceptor π-conjugated copolymers, P(DPP-BDT) and P(DPP-ANT), were synthesized in 87-89% yield. Thin-film transistors (TFTs) made from the thermally annealed film of P(DPP-ANT) exhibited much better performance (e.g., μ_max = 1.90 cm² V^-1 s^-1, I_on/off ≈ 10⁶) than those made from the thermally annealed film of P(DPP-BDT).

Chemical Communications (Cambridge, United Kingdom) published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Category: naphthyridine.

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

Gole, Bappaditya published the artcileSupramolecular polymer for explosives sensing: role of H-bonding in enhancement of sensitivity in the solid state, HPLC of Formula: 18512-55-5, the publication is Chemical Communications (Cambridge, United Kingdom) (2011), 47(36), 10046-10048, database is CAplus and MEDLINE.

A π-electron rich supramol. polymer as an efficient fluorescent sensor for electron deficient nitroarom. explosives was synthesized, and the role of H-bonding in dramatic amplification of sensitivity/fluorescence quenching efficiency in the solid state is established.

Chemical Communications (Cambridge, United Kingdom) published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, HPLC of Formula: 18512-55-5.

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

Ried, Walter published the artcileEthynation reactions. IX. Aromatic diethynylhydrocarbons and the action of hydrogen halides on diethynyl-p-benzoquindiol, Recommanded Product: 9,10-Diethynylanthracene, the publication is Chemische Berichte (1958), 2472-9, database is CAplus.

Diethynylquindiols (I) are reduced by ZnCl₂ or HI to aromatic diethynylhydrocarhons which are light-sensitive; some of them show fluorescence. The reaction of diethynyl p-benzoquindiol (1,4-dihydroxy-1,4-diethynyl-2,5-cyclohexadiene) (II) with HI or HBr yields in addition to diethynylbenzene, several halogen-containing rearrangement products. p-Benzoquinone (40 g.) in 1 l. dry Et₂O added with stirring at -35 to -40° with stirring to LiCCH from 6 g. Li in 500 cc. liquid NH₃, the mixture neutralized after 5-8 hrs. with 60 g. solid NH₄Cl, the NH₃ evaporated, and filtered, the residue extracted with three 300-cc. portions EtOAc, and the combined filtrate and extract evaporated on the water bath yielded about 16 g. II, m. 192-5° (1:1:1 C₆H₆-ligroine-dioxane) (the diethynyl hydrocarbons frequently decompose explosively above 100°; their solutions are best evaporated on a water bath). II (16 g.) in solution added at 40-5° dropwise with stirring to 45 g. SnCl₂.2H₂O in 50 cc. 50% aqueous AcOH, stirred 10 min. at 45°, cooled, and filtered, and the residue washed with H₂O yielded 5.6 g. p-C₆H₄(CCH)₂ (III), yellowish leaflets, m. 95° (dilute EtOH or petr. ether); the original filtrate diluted with 2N HCl and extracted with Et₂O, and the extract worked up gave an addnl. 1.7 g. III. III (0.5 g.) in 20 cc. 90% AcOH refluxed 4 hrs. with 250 mg. Hg(OAc)₂ and 0.1 cc. concentrated H₂SO₄, cooled. treated with 40 cc. H₂O, and neutralized with aqueous Na₂CO₃, and the product isolated with Et₂O yielded 0.5 g. p-C₆H₄Ac₂, m. 108-10° (EtOH). 2,3,5,6-Tetrachloro-1,4-dihydroxy-1,4-diethynyl-2,5-cyclohexadiene (5 g.) in 25 cc. MeOH added with stirring at 70° to 10 g. SnCl₂.2H₂O in 20 cc. concentrated HCl, stirred 10 min. at 70°, cooled, and filtered, the residue washed with H₂O and dissolved in 70 cc. hot MeOH and filtered, and the boiling filtrate diluted with H₂O to turbidity and cooled gave 1 g. p-C₆Cl₄(CCH)₂, needles which turn brown above 100°, change the crystal form at 130-40°, and show no definite m.p. 1,4-Dihydroxy-1,4-diethynyl-1,4-dihydronaphthalene (4.2 g.) in 25 cc. EtOH added at 30-5° to 9 g. SnCl₂.2H₂O in 25 cc. 50% AcOH, stirred 10 min. at 30-5°, treated with 40 cc. 2N HCl, cooled in ice, and filtered, the residue washed with H₂O and dissolved in warm petr. ether, the solution evaporated, the residue dissolved at 50° in MeOH, and the solution treated with C, diluted hot with H₂O to turbidity, and cooled deposited 49% 1,4-C₁₀H₆(CCH)₂ (IV), yellowish, light-sensitive needles, m. 60°. Solid 2,3-dichloro-1,4-naphthoquinone (40 g.) and 100 cc. dry PhMe added with stirring at -40° to LiCCH from 3 g. Li in 300 cc. liquid NH₃, the mixture neutralized after 18 hrs. with 30 g. NH₄Cl, the NH₃ evaporated, the residue extracted with three 300-cc. portions boiling EtOAc, and the extract worked up yielded 2,3-dichloro-1,4-dihydroxy-1,4-diethynyl-1,4-dihydronaphthalene (V), prisms, m. 184-5° (1:1:1 C₆H₆-ligroine-dioxane, then dilute EtOH). V (5 g.) in 25 cc. MeOH added with stirring at 50° to 10 g. SnCl₂.2H₂O in 30 cc. 50% AcOH, heated 10 min. at 65°, cooled in ice, and filtered, and the crystalline residue recrystallized from ligroine, b. 70-90°, and then 80% EtOH yielded 1 g. 2,3-di-Cl derivative (VI) of IV, light-sensitive needles which turn rapidly violet (even in the dark), decompose 135° with flashing; after prolonged storage, the decomposition point had changed to 151°. V (1.5 g.) in 20 cc. MeOH refluxed 5 min. with 10 cc. 2N HI, cooled, and extracted with Et₂O, and the extract washed with aqueous Na₂S₂O₃ and evaporated yielded about 80% crude VI. VI hydrogenated over Raney Ni in EtOAc yielded 2,3,1,4-Cl₂C₁₀H₄Et₂, pale yellow prisms, m. 92-3° (Me₂CO). 9,10-Dihydroxy-9,10-diethynyl-9,10-dihydroanthracene (VII) (2.6 g.) in 25 cc. EtOH added with stirring at 5-10° to 5 g. SnCl₂.2H₂O in 50 cc. 50% AcOH and filtered after 10 min., the residue washed with H₂O and dissolved at 50 in 100-50 cc. Me₂CO, the solution filtered and diluted with H₂O precipitated 9,10-diethynylanthracene (VIII), yellow needles which turned golden-yellow in light and then black-brown, changed at 86-8° to a brown-black solid which did not melt up to 300°. VII (2.6 g.) in 25 cc. MeOH treated with stirring at 5-10° with 10 cc. 2N HI, stirred 10 min. with cooling, and filtered gave VIII. VIII hydrogenated over Raney Ni in EtOAc gave 9,10-diethylanthracene, yellow prisms, m. 145° (MeOH-Me₂CO). 9,10-Dihydroxy-9,10-diethynyl-9,10-dihydrophenanthrene (13 g.) in 100 cc. EtOH added at 60° with stirring to 22.5 g. SnCl₂.2H₂O in 45 cc. concentrated HCl and 30 cc. H₂O, the mixture kept 1 hr. at 60-5° and cooled to room temperature, and the precipitate dried on a clay plate, digested with 5-10 cc. CCl₄, and recrystallized from hot CCl₄ or C₆H₆ yielded 3 g. 9,10-diethynylphenanthrene, needles or leaflets, which turned brown above 100° and decompose spontaneously at 130°. 1,4-Dihydroxy-1,4-bis(phenylethynyl)-2,5-cyclohexadiene (2 g.) in 30 cc. MeOH added to 3 g. SnCl₂.2H₂O in 100 cc. 50% AcOH, stirred 1 hr. at room temperature and 2 hrs. at 50-60°, cooled, diluted with 200 cc. H₂O and 20 cc. concentrated HCl, and extracted with Et₂O, and the residue from the extract recrystallized from ligroine yielded 50-60% p-C₆H₄(CCPh)₂, m. 181-2°. 1,4-Dihydroxy-1,4-bis(3-methoxy-1-propynyl)-2,5-cyclohexadiene (IX) (50 g.) in MeOH added with stirring to 100 g. SnCl₂.2H₂O in 250 cc. 50% AcOH, stirred 2 hrs. at 60°, and filtered, the MeOH evaporated in vacuo, the residual mixture diluted with 700 cc. EtOAc and treated with about 100 g. CaCl₂, the EtOAc layer neutralized with NaHCO₃ and filtered, the residue washed with EtOAc, the combined filtrate dried and evaporated, the oily residue rubbed, the crystalline deposit filtered off, the viscous filtrate distilled under N, the distillate, b_0.7 145-55°, allowed to stand, the new crystalline deposit filtered off, and the combined filter residues digested with MeOH gave 70% (crude) p-(MeOCH₂CC)₂C₆H₄, m. 42-3° (cyclohexane); the MeOH filtrate worked up gave a small amount 2,4-(MeOCH₂CC)₂C₆H₃OH (X), m. 94° (ligroine). IX treated with warm 50% AcOH gave good yields of X. 9,10-Dihydroxy-9,10-bis(phenylethynyl)-9,10-dihydrophenanthrene (1 g.) in MeOH added to 3 g. SnCl₂.2H₂O in 100 cc. 50% AcOH, heated on the water bath, and filtered, and the residue recrystallized from ligroine yielded 80% 9,10-bis(phenylethynyl)phenanthrene, needles, m. 157° (MeOH). I (4 g.) in 30 cc. MeOH added dropwise to 130 cc. 7% HI, and heated 20 min. at 60-70°, the aqueous layer extracted with Et₂O, the combined organic layers evaporated, and the residual oil heated on the water bath at 12 mm. sublimed 10% p-C₆H₄(CCH)₂ and left 60-5% oily p-AcC₆H₄CCH; 2,4-dinitrophenylhydrazone, dark red, m. 210°. II (2 g.) in 40 cc. H₂O treated at 80° with 10 cc. 250% HI, kept 5 min. at 80°, cooled, and extracted with Et₂O, the extract washed with aqueous Na₂S₂O₃, dried, and evaporated, and the residue warmed with 20 cc. petr. ether, cooled, and filtered, and the filtrate evaporated gave p-CHCC₆H₄CI:CHI, pale yellow needles, m. 74-5° (80% EtOH). II (5 g.) in 70 cc. MeOH added dropwise with stirring to 150 cc. 7% HBr, stirred 10 min. at room temperature and 0.5 hr. at 60-70°, the aqueous layer extracted with Et₂O, and the combined organic layers worked up gave 50-60% p-CHCC₆H₄COCH₂Br (XI), needles, m. 46-8° (aqueous MeOH); 2,4-dinitrophenylhydrazone, yellow crystals, decompose 180-90°. XI (1 g.) in 10 cc. MeOH refluxed 2 hrs. with 30 cc. 10% aqueous KCN and distilled, and the residue acidified yielded 100% p-CHCC₆H₄COCH₂CN, m. 184°; 2,4-dinitrophenylhydrazone, orange-yellow about 160°. II (3.2 g.) and 40 cc. 25% HBr heated 5 min. with stirring at 80°, the precipitated oil extracted into Et₂O, the solution washed and evaporated, and the residue heated with 90% aqueous MeOH and C and filtered yielded 1.7 g. p-CHCC₆H₄CBr: CHBr, pale yellow needles, m. 64-5°.

Chemische Berichte published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Recommanded Product: 9,10-Diethynylanthracene.

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

Ried, W. published the artcileEthynylation reactions. V. Aromatic diethynylhydrocarbons, SDS of cas: 18512-55-5, the publication is Angewandte Chemie (1958), 270, database is CAplus.

cf. preceding abstract 1,4-Diethynyl-1,4-dihydroxy-2,5-cyclohexadiene was reduced to 1,4-diethynylbenzene (I), m. 95°, and 9,10-diethynyl-9,10-dihydroxy-9,10-dihydroanthracene to 9,10-diethynylanthracene (II), yellow needles changing at 86-88° to a brown-black nonmelting substance. As reducing agents SnCl₂, Na dithionite, and TiCl₃ were used. I and II are fluorescent and light-sensitive. I + HCHO + Et₂NH gave a Mannich base, light yellow oil, b_0.4 108-10°; HCl salt, m. 187-8°.

Angewandte Chemie published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, SDS of cas: 18512-55-5.

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

Morisaki, Yasuhiro published the artcileSynthesis of Anthracene-Stacked Oligomers and Polymer, Category: naphthyridine, the publication is Organic Letters (2010), 12(14), 3188-3191, database is CAplus and MEDLINE.

Anthracene-stacked oligomers and a polymer were synthesized using a xanthene skeleton as the scaffold, and their structures and properties were fully characterized. Intramol. π-π stacking of the anthracene rings in the ground state and excited state was observed

Organic Letters published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, Category: naphthyridine.

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

Kang, Hyun Suk published the artcileConjugated-linker dependence of the photophysical properties and electronic structure of chlorin dyads, SDS of cas: 18512-55-5, the publication is Journal of Porphyrins and Phthalocyanines (2021), 25(7/8), 639-663, database is CAplus.

The synthesis, photophys. properties and electronic structure of seven new chlorin dyads and associated benchmark monomers are described. Each dyad contains two identical chlorins linked at the macrocycle β-pyrrole 13-position. The extent of electronic communication between chlorin constituents depends on the nature of the conjugated linker. The communication is assessed by modification of prominent ground-state absorption and redox properties, rate constants and yields of excited-state decay processes, and mol.-orbital characteristics. Relative to the benchmark monomers, the chlorin dyads in toluene exhibit a substantial bathochromic shift of the long-wavelength absorption band (30 nm average), two-fold increased radiative rate constant [average (10 ns)^-1 vs. (22 ns)^-1], reduced singlet excited-state lifetimes (average 5.0 ns vs. 8.2 ns), and increased fluorescence quantum yields (average 0.56 vs. 0.42). The excited-state lifetime and fluorescence yield for the chlorin dyad with a benzothiadiazole linker are reduced substantially in benzonitrile vs. toluene due largely to ∼ 25-fold accelerated internal conversion. The results aid design strategies for mol. architectures that may find utility in solar-energy conversion and photomedicine.

Journal of Porphyrins and Phthalocyanines published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C18H10, SDS of cas: 18512-55-5.

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

Zhu, Jikai published the artcileSynthesis and self-assembly of oligomers containing cruciform 9,10-bis(arylethynyl)anthracene unit: formation of supramolecular nanostructures based on rod-length-dependent organization, HPLC of Formula: 18512-55-5, the publication is Tetrahedron (2014), 70(6), 1230-1235, database is CAplus.

Conjugated rod-coil mols., incorporating flexible and rigid blocks, have a strong affinity to self-organize into various supramol. nanostructures in the bulk state.In this study, we report synthesized oligomers containing cruciform 9,10-bis(arylethynyl)anthracene units and characterized their self-assembly behavior. The mol. structures were characterized with ¹H, ¹³C NMR, and matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectroscopy. An investigation of the supramol. nanostructures of these mols. using differential scanning calorimetry, thermal polarized optical microscopy, and small-angle X-ray scattering revealed that the rod length of coil-rod-coil mols. with identical rod to coil volume ratios dramatically influences self-assembly behavior in the bulk state.

Tetrahedron published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C15H14O3, HPLC of Formula: 18512-55-5.

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

Yang, Wenbo published the artcileDirect Observation of Long-Lived Upper Excited Triplet States and Intersystem Crossing in Anthracene-Containing Pt^II Complexes, SDS of cas: 18512-55-5, the publication is Journal of Physical Chemistry Letters (2019), 10(24), 7767-7773, database is CAplus and MEDLINE.

Exceptionally long-lived T₂ states (7 ns) were observed with the N^N Pt^II bisacetylide complex (Pt-1) and trans-bis(phosphine) Pt^II bisacetylide complexes (Pt-2, Pt-3) containing anthryl acetylide ligands. For Pt-1, fluorescence of the anthryl moiety (An) was quenched and phosphorescence was observed Under 350 nm excitation, the upper long-lived triplet state T₂ (³An) was populated via ultrafast intersystem crossing (ISC) of S₁ (¹An) → T₂ (³An) (within 0.2 ps). Interestingly, Pt-3, after population of the S₁ state, emits strong fluorescence (Φ_F = 89%); the poor ISC is due to the high-lying T₂ (³An, 3.36 eV) vs. S₁ (¹An, 2.55 eV) state and the large energy gap between S₁ (¹An, 2.55 eV) and T₁ (³An, 1.32 eV) states. The population of the upper excited state S₂ (¹LLCT, 3.49 eV) turns to an efficient S₂ → T₂ → T₁, and ISC yield increases by 55% compared with S₀ → S₁ excitation. These results present new in-depth insights into fundamental photochem. of upper excited states.

Journal of Physical Chemistry Letters published new progress about 18512-55-5. 18512-55-5 belongs to naphthyridine, auxiliary class Alkynyl,Anthracene, name is 9,10-Diethynylanthracene, and the molecular formula is C42H63O3P, SDS of cas: 18512-55-5.

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