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Hydrogen-bond self-assembly super-molecular blue-fluorescence polymer and symmetric method thereof

A technology of blue fluorescence and synthesis method, applied in the field of pyrazoline compounds, can solve problems such as poor performance of electroluminescent devices, and achieve the effects of improving connection strength, improving fluorescence quantum yield, and increasing bonding strength

Inactive Publication Date: 2010-04-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this type of fluorescent unit generally has a high fluorescence quantum efficiency, the relative fluorescence quantum efficiency of the final blue supramolecular polymer in solution is only 0.5, so the electroluminescent device made of this supramolecular polymer [See (10) Abbel R, Grenier C, Meijer E W, Schenning A P H J, et al.J.Am.Chem.Soc., 2009, 131, 833]

Method used

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  • Hydrogen-bond self-assembly super-molecular blue-fluorescence polymer and symmetric method thereof
  • Hydrogen-bond self-assembly super-molecular blue-fluorescence polymer and symmetric method thereof
  • Hydrogen-bond self-assembly super-molecular blue-fluorescence polymer and symmetric method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Supramolecular polymer 1 and its synthesis:

[0089] The synthetic process step of supramolecular polymer 1 comprises following three steps: (1) synthetic N-carboxymethyl {2-octyloxy group-5-[N-(2-acetamidoacetyl) amino] benzamide }(fragment I); (2) synthesis of 3,5-diamino-N-{4-[1-phenyl-3-(4-methylphenyl)-4,5-dihydro-1H-pyrazole -5-yl] phenyl} benzamide (fragment II-1); (3) link fragment I and fragment II-1 into monomer molecule 1, and self-assemble into supramolecular polymer 1.

[0090] 1. Synthesis of Fragment I

[0091] Fragment I was successfully prepared from methyl salicylate as raw material through eight steps of reaction and seven intermediates including Ia, Ib, Ic, Id, Ie, If, and Ig. Among them, the process steps (1) to (6) of the first six steps of reaction, that is, the synthesis process steps of intermediates Ia, Ib, Ic, Id, Ie, If, can be found in Chinese invention patent ZL200410081544.1, patent application date: 2004 December 21.

[0092] (7) Synth...

Embodiment 2

[0113] Supramolecular polymer 2 and its synthesis:

[0114] The synthesis process step of supramolecular polymer 2 comprises following three steps: (1) synthetic N-carboxymethyl {2-octyloxy group-5-[N-(2-acetamidoacetyl) amino] benzamide }(fragment I); (2) synthesis of 3,5-diamino-N-{4-[1-phenyl-3-(4-ethylphenyl)-4,5-dihydro-1H-pyrazole -5-yl] phenyl} benzamide (fragment II-2); (3) link fragment I and fragment II-2 into monomer molecule 2, and self-assemble into supramolecular polymer 2.

[0115] The synthesis process steps of Fragment I are the same as in Example 1; the synthesis process steps of Fragment II-2 are similar to the synthesis process steps of Example 1 Fragment II-1, only the raw material is replaced by ethylbenzene (IIa-1) by toluene (IIa-1) 2); the synthesis process steps of linking fragment I and fragment II-2 into monomer molecule 2 and self-assembling into supramolecular polymer 2 are the same as in Example 1, only replacing II-1 with II-2. The obtained sup...

Embodiment 3

[0117] Supramolecular polymer 3 and its synthesis:

[0118] The synthetic process step of supramolecular polymer 3 comprises following three steps: (1) synthetic N-carboxymethyl {2-octyloxy group-5-[N-(2-acetamidoacetyl) amino] benzamide } (fragment I); (2) synthesis of 3,5-diamino-N-{4-[1-phenyl-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyridine Azol-5-yl]phenyl}benzamide (fragment II-3); (3) link fragment I and fragment II-3 into monomer molecule 3, and self-assemble into supramolecular polymer 3.

[0119] The synthesis process steps of Fragment I are the same as in Example 1; the synthesis process steps of Fragment II-3 are similar to the synthesis process steps of Example 1 Fragment II-1, only the raw material is replaced by anisole (IIa-1) by toluene (IIa-1) -3); The synthesis process steps of linking fragment I and fragment II-3 into monomer molecule 3 and self-assembling into supramolecular polymer 3 are the same as in Example 1, only replacing II-1 with II-3. The obtained su...

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Abstract

The invention relates to a pyrazoline-type hydrogen-bond self-assembly super-molecular polymer with blue-fluorescence property. The invention adopts an oligo-polyamide strip without secondary repulsion force as a hydrogen-bond bonding part and increases the number of hydrogen-bond donors and hydrogen-bond receptors to 8 from 4 so as to greatly improve the connection strength of the polymer. In addition, a pyrazoline derivative is introduced in a super-molecular polymer monomer as a blue-fluorescence unit to obtain a super-molecular blue-fluorescence polymer with a higher fluorescence quantum yield. The obtained six novel super-molecular polymer blue-fluorescence materials can emit pure-blue fluorescence in a solution state and have emission wavelengths of 440-455nm, semi-peak widths of 61-70nm and better color purity and can emit pure-blue fluorescence in a solid state and have emission wavelengths of 451-474nm, semi-peak widths of 71-79nm and better color purity.

Description

technical field [0001] The present invention relates to a class of pyrazoline compounds with blue fluorescent properties, in particular to a class of supramolecular polymer blue fluorescent compounds with pyrazoline fluorescent units obtained through hydrogen bond self-assembly. The present invention also relates to The synthesis method of this kind of compound. Background technique [0002] Supramolecular polymers are constructed by non-covalent bonding forces such as hydrogen bonds, coordination bonds, electrostatic attraction, hydrophobic interactions, host-guest interactions, van der Waals forces, and π-π stacking interactions. A special polymer that combines highly oriented forces and exhibits polymer properties in solution or in bulk [see (1) Brunsveld L, Folmer B J B, Meijer E W, Chem. Rev., 2001, 101, 4071]. [0003] Among all the supramolecular interactions, hydrogen bonding has attracted extensive attention due to its moderate bonding energy and specific recogniti...

Claims

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Application Information

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IPC IPC(8): C08G69/12C09K11/06C07C237/44C07C231/12C07D231/06
Inventor 雷光东卢志云邱德敏黄艳
Owner SICHUAN UNIV
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