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Thiophene [3,4-b] thiophene panchromatic fluorescent dye as well as preparation method and application thereof

A fluorescent compound, n-o technology, applied in the field of full-color fluorescent dyes and their preparation, can solve problems such as the reduction of fluorescence quantum yield

Active Publication Date: 2017-11-28
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For most organic conjugated fluorescent dyes, as the polarity of the solvent increases, the fluorescence quantum yield decreases rapidly

Method used

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  • Thiophene [3,4-b] thiophene panchromatic fluorescent dye as well as preparation method and application thereof
  • Thiophene [3,4-b] thiophene panchromatic fluorescent dye as well as preparation method and application thereof
  • Thiophene [3,4-b] thiophene panchromatic fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1: the preparation of TbT-PhH

[0071]

[0072] One of the preparation methods of compound TbT-PhH: Dissolve compound 1 (212mg, 1mmol) and monobromobenzene 2 (345mg, 2.2mmol) in dry DMF (5ml), and add K 2 CO 3 (331mg, 2.4mmol), triphenylphosphine (26mg, 0.1mmol), palladium acetate (11.2mg, 0.05mmol), heated under reflux for 24h under dark conditions. Cooled to room temperature, extracted with dichloromethane, dried the organic phase with magnesium sulfate, and spin-dried, the crude product was chromatographed to obtain 326 mg of the desired product as a pale yellow solid with a yield of 85%. 1 H NMR (400MHz, CDCl 3 )δ7.98(s,1H),7.69-7.73(m,4H),7.45-7.50(m,4H),7.38(t, 3 J=7.2Hz,1H),7.32(t, 3 J=7.2Hz,1H),4.41(q, 3 J=7.2Hz, 2H), 1.42(t, 3 J=7.2Hz,3H).

[0073]

[0074] The second preparation method of compound TbT-PhH: Dissolve compound 3 (212mg, 1mmol) and phenylboronic acid 4 (268mg, 2.2mmol) in dry 1,4-dioxane (5ml), under inert gas protection co...

Embodiment 2

[0077] Embodiment 2: Preparation of TbT-PhMe

[0078]

[0079] The preparation method is basically the same as in Example 1, except that the substrate monobromobenzene is replaced by 4-methylbromobenzene, and the product is a light yellow solid with a yield of 81%. 1 H NMR (300MHz, CDCl 3 )δ7.96(s,1H),7.59(m,4H),7.27(m,4H),4.40(q, 3 J=5.4Hz, 2H), 2.41(s, 3H), 2.39(s, 3H), 1.42(t, 3 J=5.4Hz,3H).

Embodiment 3

[0080] Embodiment 3: the preparation of TbT-PhOMe

[0081]

[0082] The preparation method is basically the same as in Example 1, except that the substrate monobromobenzene is replaced by 4-methoxybromobenzene, and the product is a yellow solid with a yield of 60%. 1 H NMR (300MHz, CDCl 3 )δ7.92(s,1H),7.59-7.63(m,4H),6.98-7.00(m,4H),4.40(q, 3 J=5.4Hz, 2H), 3.87(s, 3H), 3.86(s, 3H), 1.42(t, 3 J=5.4Hz,3H).

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Abstract

The invention relates to a thiophene [3,4-b] thiophene panchromatic fluorescent dye as well as a preparation method and an application thereof. The invention provides a thiophene [3,4-b] thiophthene aryl substituted compound which has a panchromatic luminance property and high fluorescence quantum yield in a strongly aprotic solvent, and further provides a preparation method which is capable of synthesizing the compound greenly and efficiently through a one-step reaction, is low in production cost and has industrial production potential. The method comprises a C-H direct arylation reaction and a Suzuki-miyara or Stille cross coupling reaction; and meanwhile the compound can be applied to medicinal diagnosis, disease treatment, luminescent layers of white light or organic light emitting diodes, and the like.

Description

technical field [0001] The present invention relates to a class of full-color fluorescent dyes and their preparation methods and applications, in particular to a class of thiophene[3,4-b]thiophene-based fluorescent compounds and their preparation methods and applications. Background technique [0002] Organic conjugated fluorescent dyes are widely used in sensing, bioimaging technology, and organic light-emitting diodes (OLEDs) due to their high fluorescence quantum yield and their fluorescence properties can be precisely regulated by molecular structure design (Applied Fluorescence in Chemistry, Biology, and Medicine, (Eds.: W. Rettig, B. Strehmel, S. Schrader, H. Seifert), Springer: New York, 1999; A.P. deSilva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, T.E. Rice, Chem. Rev. 1997, 97, 1515-1566; L.D. Lavis, R.T. Raines, ACS Chem. Biol. 2014, 9, 855-866). Fluorescent dyes have received extensive attention in the diagnosis and treatment ...

Claims

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Application Information

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IPC IPC(8): C07D495/04C09B57/00C09K11/06H01L51/54G01N21/64G01N21/33
CPCG01N21/33G01N21/6486C09K11/06C07D495/04C09B57/00C09K2211/1007C09K2211/1092H10K85/6576H10K50/11
Inventor 朱晓张刘峰
Owner INST OF CHEM CHINESE ACAD OF SCI