Novel red light emitting 9,10-bis(phenylethynyl)anthracenes

Abstract

Novel 9,10-bis(phenylethynyl)anthracenes (BPEA's) 5 were prepared in high yields and purity. They were synthesized by a Pd-catalyzed Sonogashira coupling reaction. These compounds are typical intramolecular charge transfer compounds, which consist of the electron-rich anthracene moiety and an electron acceptor part. Their emissions are all in the red region with λ max ranging between 616-638 nm and they exhibit high fluorescent quantum efficiencies.

Tuning of dye optical properties by environmental effects: a QM/MM and experimental study

“…According to a literature procedure, 35 4-(5-((4-ethoxyphenyl)ethynyl)-1-methyl-1H-imidazol-2-yl)benzaldehyde (64 mg, 0.2 mmol) was reacted with malononitrile (20 mg, 0.3 mmol) in EtOH (7 mL) and a catalytic amount (5 drops) of triethylamine. The reaction mixture was stirred at room temperature for 12 h, then concentrated under reduced pressure to obtain the required product as a bright orange powder (60 mg, 83% yield): m.p.…”

Synthesis and Electronic Properties of Length-Defined 9,10-Anthrylene–Butadiynylene Oligomers

“…Found: C, 81.19; H, 10.06. 2,6-Di- tert -butyl-9,10-bis­[(trimethylsilyl)­ethynyl]­anthracene ( 6 ) was prepared in a similar manner from 2,6-di- tert -butyl-9,10-anthraquinone and [(trimethylsilyl)­ethynyl]­acetylene. Compound 6 : yellow green solid, yield 87%; R f 0.32 (hexane); mp 232–234 °C; 1 H NMR (500 MHz, CDCl 3 ) δ 0.44 (s, 18H), 1.50 (s, 18H), 7.72 (dd, J = 9.0, 2.0 Hz, 2H), 8.51 (d, J = 2.0 Hz, 2H), 8.52 (d, J = 9.5 Hz, 2H); 13 C NMR (125 MHz, CDCl 3 ) δ 0.2, 30.8, 35.2, 101.9, 107.5, 117.5, 121.5, 126.2, 126.8, 130.8, 132.1, 149.0; HRMS (FAB) m / z calcd for C 32 H 42 Si 2 [M] + 482.2825, found 482.2802.…”

“…A mixture of 9-[(triisopropylsilyl)­ethynyl]-10-[(trimethylsilyl)­ethynyl]­anthracene ( 5 ( H ), 66.5 mg, 0.146 mmol) and 9,10-bis­[(trimethylsilyl)­ethynyl]­anthracene ( 6 ( H ), 54.2 mg, 0.146 mmol) was treated with K 2 CO 3 (201 mg, 1.46 mmol, 10 equiv) in THF (16 mL) and MeOH (16 mL) at room temperature for 1.5 h in the dark. To the solution were added PdCl 2 (PPh 3 ) 2 (15.5 mg, 22 μmol, 0.15 equiv), CuI (4.1 mg, 22 μmol, 0.15 equiv), I 2 (28 mg, 0.11 mmol, 0.75 equiv), and ( i -Pr) 2 NH (16 mL) under air.…”

A one-pot synthesis of oligo(arylene–ethynylene)-molecular wires and their use in the further verification of molecular circuit laws

“…To overcome these various inconveniences, a number of procedures have been developed for the preparation of OAE compounds based on the in situ deprotection of bis(trimethylsilylethynyl) arylenes (Me 3 SiC≡CArC≡CSiMe 3 ) prior to coupling with an arylhalide. [53,[56][57][58][59] Various desilylating agents have been employed, including catalytic hexafluorosilicic acid, [60] or more commonly tetrabutylammonium fluoride (TBAF), [61,62] CsF, [63] and various nucleophilic bases. [64] The main disadvantage of TBAF-facilitated desilylations is the subsequent difficulty in the purification of the desired products, free of ionic side products.…”