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Synlett

Volumn , Issue 2, 2007, Pages 231-234

Synthesis and spectroscopic studies of various arylene ethynylene fluorophores

(5) Shao, Guang a Orita, Akihiro a Taniguchi, Hisataka a Ishimaru, Kanako a Otera, Junzo a

a OKAYAMA UNIVERSITY OF SCIENCE (Japan)

Author keywords

Alkynes; Eliminations; Sldehydes; Spectroscopy; Sulfones

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; AROMATIC COMPOUND; FLUORESCENT DYE; FLUOROPHORE DERIVATIVE; IODODIPHENYLETHYNE; PHENELYNE ETHYNYLENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ELIMINATION REACTION; PHOTOLUMINESCENCE; SOLID STATE; SONOGASHIRA REACTION; SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 33847063905 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968015 Document Type: Article

Times cited : (10)

References (17)

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3
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- and references therein
- (c) Balakrishnan, K.; Datar, A.; Zhang, W.; Yang, X.; Naddo, T.; Huang, J.; Zuo, J.; Yen, M.; Moore, J. S.; Zang, L. J. Am. Chem. Soc. 2006, 128, 6576; and references therein.
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10
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11
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12
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13
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14
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- A part of optical property of 4-(4-methoxyphenylethynyl)phenylethyne has been reported. See: Shao, G.; Orita, A.; Nishijima, K.; Ishimaru, K.; Takezaki, M.; Wakamatsu, K.; Otera, J. Chem. Lett. 2006, 35, 1284.
- A part of optical property of 4-(4-methoxyphenylethynyl)phenylethyne has been reported. See: Shao, G.; Orita, A.; Nishijima, K.; Ishimaru, K.; Takezaki, M.; Wakamatsu, K.; Otera, J. Chem. Lett. 2006, 35, 1284.

15
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16
- 33847035518
- Double Elimination Method for 1 and 7: 1-(3,7-Dimethyloctyloxy)-4-(4- ethynylphenylethynyl)benzene(1, To a THF solution (15 mL) of 4-(3,7-dimethyloctyloxy)phenylmethyl phenyl sulfone (3, 466 mg, 1.2 mmol, 4-(trimethylsilylethynyl)benzaldehyde (4, 202 mg, 1.0 mmol) and diethylchlorophosphate (0.17 mL, 1.2 mmol) was added a THF solution of LiHMDS (1.0 M, 5.0 mL, 5.0 mmol) at 0°C, and the mixture was stirred at r.t. for 16 h under argon. After usual work-up, the organic layer was evaporated and the residue was subjected to a column chromatography on silica gel (10% EtOAc-hexane) to give 1-(3,7-dimethyloctyloxy)-4, 4-(trimethylsilylethynyl) phenylethynyl]benzene in a pure form (358 mg, 83, To a solution of 1-(3,7-dimethyloctyloxy)-4-[4-(trimethylsilylethynyl)phenylethynyl]benzene (2.15 g, 5.0 mmol) in THF (25 mL) and MeOH (25 mL) was added 6.91 g of K 2CO3. The reaction mixture was stirred for 1.5 at r.t. After H2O had been add
- 3): δ = 19.6, 22.6, 22.7, 24.6, 28.0, 29.8, 36.1, 37.3, 39.2, 66.4, 87.1, 91.0, 93.6, 114.6, 114.6, 123.2, 132.9, 133.0, 137.4, 159.4.

17
- 33847024321
- Typical Procedure for Sonogashira Coupling. A 50 mL flask was charged with 7 (318 mg, 0.69 mmol, 1,4-diethyl-2,5-diethynylbenzene (55 mg, 0.30 mmol, Pd(PPh3)4 (34 mg, 0.03 mmol, CuI (5.0 mg, 0.03 mmol, i-Pr2NH (1.0 mL) and toluene (20 mL, and the mixture was heated at 65°C for 12 h. After filtration, the filtrate was poured into aq NH4Cl and extracted with CH2Cl2. The combined organic layer was washed with brine, dried over MgSO4 and filtered. After evaporation, the residue was subjected to column chromatography to afford 2a as white powder in a pure form (228 mg, 90, Compound 2a: mp 151-153°C. 1H NMR (500 MHz, CDCl 3, δ, 0.87 (d, J, 6.7 Hz, 12 H, 0.94 (d, J, 6.4 Hz, 6 H, 1.15-1.20 (m, 6 H, 1.25-1.37 (m, 12 H, 1.50-1.67 (m, 6 H, 1.82-1.85 (m, 2 H, 2.85 (q, J, 7.5 Hz, 4 H, 3.99-4.05 (m, 4 H, 6.88 d
- +]: 1157.5; found: 1157.6.

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