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Copper (I) phosphorine heterocyclic complex and preparation method and application thereof

A technology of benzene heterocycles and complexes, which is applied in the field of copper (I) phosphine benzene heterocycle complexes and its preparation, can solve the problems that the fluorescence intensity and lifetime cannot change with temperature, the temperature range is narrow, and the sensitivity is low, achieving excellent Effects of luminescence properties, high sensitivity, and excellent luminescence performance

Active Publication Date: 2018-03-13
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the defects and deficiencies of the fluorescent temperature sensor in the prior art, such as low sensitivity, narrow temperature range, and inability to change the fluorescence intensity and life with temperature, and provide a bisphosphine heterocycle with excellent luminescent properties. Phosphine copper (I) complex, at room temperature and low temperature, its lifetime is about 100 microseconds and 2 milliseconds, can emit orange phosphorescence; and its luminous intensity and lifetime can increase with the decrease of temperature High, with a high degree of temperature dependence, can be used as a molecular fluorescent probe for the preparation of fluorescent temperature sensors. The luminous intensity and lifetime of the prepared fluorescent temperature sensor show a good linear relationship with temperature, and have high sensitivity, wide linear range, etc. features

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  • Copper (I) phosphorine heterocyclic complex and preparation method and application thereof
  • Copper (I) phosphorine heterocyclic complex and preparation method and application thereof
  • Copper (I) phosphorine heterocyclic complex and preparation method and application thereof

Examples

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Embodiment 1

[0050] Example 1 Preparation of copper (I) chlorophosphine benzene heterocyclic bisphosphine complex

[0051] 1. Prepare the ligand

[0052] (1) Under nitrogen atmosphere, add (2.0g, 8.0mmol) 4,6-diphenyl-2-pyrone, (2.43 g, 8.0 mmol) [Na(OCP)·(dioxane) 2.5 ], and 50mL of anhydrous tetrahydrofuran were added to the reaction flask and heated to reflux at 90°C for 24 hours. After the reaction, cool, filter, extract with anhydrous tetrahydrofuran and anhydrous ether successively, and wash the solid with anhydrous n-hexane to obtain the corresponding intermediate product as light yellow solid powder (phen) 2 C 5 PONa. Yield: 73%. The melting point is 185°C. 1 H NMR (CD 3 CN, 400MHz): δ = 7.65 (d, 4 H, C arom ), 7.37 (t, 2 H, C arom ), 7.29 (m, 5 H, C arom &C 5 ),7.00 (d, 1 H, C 5 ); 13 C{ 1 H}NMR (CD 3 CN, 100.5 MHz): δ = 209.5 (d, C 5 ), 171.5 (d,C 5 ), 145.8(d, C 5 ) 145.2(s, C 5 ), 144.2(s, C 5 ), 128.8(d, C arom ), 127.6(s, C arom ),127.3 (d, C arom ), 127....

Embodiment 2

[0059] Example 2 Preparation of copper (I) bromophosphine benzene heterocyclic bisphosphine complex

[0060] Ligand (phen) 2 C 5 P-O-P (phen) 2 The preparation is the same as in Example 1, under nitrogen atmosphere, the ligand (18.6 mg, 0.13 mmol) (phen) 2 C 5 P-O-P (phen) 2 React with (58.0 mg, 0.13 mmol) cuprous bromide CuBr in anhydrous tetrahydrofuran for 2 hours, filter to obtain a solid, and wash the solid with anhydrous n-hexane to obtain complex 2: [(phen) 2 C 5 P-O-P (phen) 2 ] 2 [Cu 2 Br 2 ]. Yield: 87%.

[0061] Anal. Calcd for C 58 h 44 P 4 o 2 Cu 2 Br 2 : C, 58.85%; H, 3.75%; Found: C, 58.82%; H, 3.88%.

[0062] UV / Vis: λ 1 = 328 nm, λ 2 = 410nm.

[0063] IR (ATR, [cm -1 ]): 3057 (w, C-H str.), 1965 (w), 1900 (w), 1814 (w), 1777(w), 1570 (m), 1531, 1492, 1472, 1450 (m, -C 6 h 5 ), 1436 (m), 1383 (m), 1353 (w), 1334 (w), 1312 (w), 1272 (w), 1249 (w), 1184 (w), 1138 (s, C-O str.) ,1107(s), 1079(m), 1027(w), 999(w), 957(s), 915(w), 898(w), ...

Embodiment 3

[0064] Example 3 Preparation of copper (I) iodophosphine benzene heterocyclic bisphosphine complex

[0065] Ligand (phen) 2 C 5 P-O-P (phen) 2 The preparation is the same as in Example 1, under nitrogen atmosphere, the ligand (13.6 mg, 0.07 mmol) (phen) 2 C 5 P-O-P (phen) 2 React with (32.0 mg, 0.07 mmol) cuprous iodide CuI in anhydrous tetrahydrofuran for 2 hours, filter to obtain a solid, and wash the solid with anhydrous n-hexane to obtain complex 3: [(phen) 2 C 5 P-O-P (phen) 2 ] 2 [Cu 2 I 2 ]. Yield: 90%.

[0066] Anal. Calcd for C 58 h 44 P 4 o 2 Cu 2 I 2 : C, 54.52%; H, 3.47%; Found: C, 54.21%, H, 3.45%.

[0067] UV / Vis: λ 1 = 332 nm, λ 2 = 410nm.

[0068] IR (ATR, [cm -1 ]): 3054 (w, C-H str.), 1956 (w), 1900 (w), 1817 (w), 1776(w), 1570 (m), 1532, 1492, 1471, 1450 (m, -C 6 h 5 ), 1436 (m), 1381 (m), 1353 (w), 1334 (w), 1313 (w), 1271 (w), 1248 (w), 1185 (w), 1135 (s, C-O str.) ,1107(s), 1079(m), 1068(w), 1028(w), 999(w), 957(s), 917(w), 899(...

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Abstract

The invention discloses a copper (I) phosphorine heterocyclic complex and a preparation method and application thereof. The structural formula of the copper (I) phosphorine heterocyclic complex is shown in the formula I. In the formula, X represents a halogen element. The complex has good phosphorescence performances at the room temperature and 77K, lifetime of about 100 microseconds at the room temperature and lifetime of about 2 milliseconds at 77K. In a range of 77K to 297K, the lifetime of the complex has high dependence on the temperature. The lifetime of a sensor prepared from the complex has high linear dependence on the temperature. The complex has excellent sensitivity and stability and a very wide temperature response range of 77K to 337K. The invention discloses a copper (I) metal complex fluorescence temperature sensor in a visual temperature-life linear relationship. The copper (I) metal complex fluorescence temperature sensor has the advantages of low cost, simple preparation process and great application prospect.

Description

technical field [0001] The invention belongs to the technical field of material chemistry, and in particular relates to a copper (I) phosphine benzene heterocyclic complex and its preparation method and application. Background technique [0002] Temperature is a key characteristic parameter in many fields. Temperature sensors, as the earliest developed devices with rich varieties, are widely used in meteorology, aeronautics, scientific research, industry and other fields. Metal complex fluorescent temperature sensors have been extensively researched and developed due to their unique properties. They often have lifetimes on the order of microseconds, absorb in the visible range, emit fluorescence or phosphorescence, and have large Stokes shifts. These metal complex molecular probes are often sensitive to oxygen, so they are usually embedded in polymers to make membrane materials for fluorescent temperature probes. At present, most of the fluorescent temperature complexes s...

Claims

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Application Information

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IPC IPC(8): C07F1/08C09K11/06G01K11/32G01N21/64G01N21/33
CPCG01K11/32G01N21/33G01N21/643C09K11/06C07F1/005C09K2211/188
Inventor 李忠曙李雅奇苏成勇
Owner SUN YAT SEN UNIV
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