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Platinum (II) alkyne complex and application thereof

A technology of complexes and compounds, applied in the field of nonlinear optical materials

Inactive Publication Date: 2015-03-25
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the alkynyl side by introducing a naphthalimide group

Method used

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  • Platinum (II) alkyne complex and application thereof
  • Platinum (II) alkyne complex and application thereof
  • Platinum (II) alkyne complex and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of fluorene-bipyridine platinum (II) chloride complex (compound M-1)

[0023] Reaction formula:

[0024]

[0025] Add (224mg, 0.534mmol) platinum (II) chlorodimethylsulfoxide complex 2 and (438mg, 0.534mmol) 4,4'-bis(9,9-dihexylfluorenyl) to a 250mL three-necked flask Bipyridine (compound C-1), and then add 60 mL of acetonitrile and 100 mL of dichloromethane respectively. Heat to reflux for 6-8 hours, cool down to room temperature after the reaction, and spin off the solvent under reduced pressure. The obtained crude product was purified by column chromatography, and the developing solvent was dichloromethane. 290 mg of yellow solid were obtained, yield 87.2%. 1 H NMR (400MHz, CDCl 3 ): δ9.73(m, 2H), 8.22(s, 2H), 7.83(d, J=7.8Hz, 2H), 7.73(d, J=2.5Hz, 6H), 7.64(s, 2H), 7.33 (m, 6H), 2.01-1.97 (m, 8H), 1.05-0.96 (m, 24H), 0.67 (t, J=6.9Hz, 12H,), 0.60-0.56 (m, 8H). 13 C NMR (400MHz, CDCl 3 )δ (ppm): 153.8, 150.5, 148.3, 147.8, 143.1...

Embodiment 2

[0026] Embodiment 2: the synthesis of compound T-1

[0027] Reaction formula:

[0028]

[0029]In the three-necked flask of 250mL, add (145mg, 0.134mmol) compound M-1, (92mg, 0.333mmol) N-butyl-6-ethynyl naphthalimide (compound N-Bu-NI≡) and ( 6mg, 0.003mmol) of cuprous iodide, and then added 50mL of anhydrous diisopropylamine and 90mL of anhydrous dichloromethane. Heating to reflux under nitrogen protection for 20-24 hours, after the reaction was completed, it was cooled to room temperature, and the solvent was rotated off under reduced pressure. The obtained crude product was purified by column chromatography, and the developing solvent was dichloromethane:petroleum ether=1:1. 122 mg of a red solid was obtained, yield 58.2%. 1 H NMR (400MHz, CDCl 3 ): δppm 9.87(d, J=5.9Hz, 2H), 9.21(d, J=8.3Hz, 2H), 8.58-8.49(m, 6H), 8.00-7.75(m, 12H), 7.56(t, J =7.8Hz, 2H), 7.43(d, J=2.9Hz, 6H), 4.21(t, J=7.6Hz, 4H), 2.09-2.05(dd, J=10.7Hz, J=5.4Hz, 8H), 1.79-1.72(m, 4H), 1.53-1.4...

Embodiment 3

[0030] Embodiment 3: the synthesis of carbazole-bipyridine platinum (II) chloride complex (compound M-2)

[0031] Reaction formula:

[0032]

[0033] The process was the same as in Example 1, except that the reactant C-1 was replaced with 4,4'-bis(N-hexylcarbazolyl)bipyridine (compound C-2).

[0034] The obtained crude product was purified by column chromatography, and the developing solvent was dichloromethane. A yellow solid was obtained in a yield of 91.2%. 1 H NMR (400MHz, CDCl 3 ): δ8.91(s, 2H), 8.82-8.81(d, J=5.0Hz, 2H), 8.58(s, 2H), 8.24-8.22(d, J=3.8Hz, 2H), 7.94-7.91( dd, J=4.3Hz, 2H), 7.72-7.70(dd, J=2.5Hz, 2H), 7.54-7.43(m, 6H), 7.33-7.29(t, J=3.7Hz, 2H), 4.33-4.29 (t, J=4.0Hz, 4H), 1.93-1.86(m, 4H), 1.41-1.28(m, 12H), 1.07-1.05(m, 16H), 0.91-0.87(t, J=3.4Hz, 12H ). 13 C NMR (400MHz, CDCl 3 ):156.82,150.21,149.60,141.01,140.97,128.90,126.11,124.95,123.50,122.95,121.61,119.31,119.25,119.10,109.16,109.02,43.27,31.61,29.00,27.01,22.60,14.08.Elemental analysi...

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Abstract

The invention provides a platinum (II) alkyne complex and application thereof. The platinum (II) alkyne complex is structurally a platinum (II) alkyne naphthalene imide compound by using bipyridine derivative as a ligand. A preparation method of the platinum (II) alkyne complex comprises the following steps: firstly, enabling potassium tetrachloroplatinate to react with dimethyl sulfoxide to obtain a potassium tetrachloroplatinate-dimethyl sulfoxide complex; secondly, enabling the potassium tetrachloroplatinate-dimethyl sulfoxide complex to react with the bipyridine ligand to a obtain bipyridine platinum (II) chloride complex; finally, performing Sonogashira reaction on the bipyridine platinum (II) chloride complex and alkyne ligand to obtain a series of the bipyridine platinum (II) alkyne naphthalene imide compounds. Test results show that the platinum complexes synthesized by the preparation method have a good optical limiting property and can be applied to nonlinear absorbent materials.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to nonlinear optical materials, which contain novel organic platinum (II) alkyne complexes. technical background [0002] In today's information age, with the rapid development of the information industry, higher requirements are put forward for information technology, signal processing technology, etc., and correspondingly higher requirements are put forward for optical materials, so it has special information processing functions and ultra-fast response. Optoelectronic materials will become the main body of the development of information materials. For the development of optoelectronic technology, nonlinear optics has played a key role. Due to their important role and application prospects in the fields of optical information processing, optical computing, optical switching and optical limiting, nonlinear optical materials have become a research hotspot in recent ye...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00G02F1/361
CPCG02F1/3611C07F15/0086
Inventor 朱红军殷治国刘睿李崇柳曹枝金晓东展秋英刘琪丁源
Owner NANJING UNIV OF TECH
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