Fluorine-perylene bisimide molecule internal-energy transferring fluorescence split compound and preparation method thereof

A fluorescent compound and perylene imide technology, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problem of low two-photon absorption ability, achieve improved absorption performance, increase frequency doubling effect, and increase charge The effect of transfer degree

Inactive Publication Date: 2014-11-19
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorescent compounds with D-π-A structure using fluorene as a donor and peryleneimide as an acceptor have not been reported.
In particular, the fluorescent molecules with the D-π-A structure reported so far are mostly coplanar large π conjugated systems, most of the intramolecular energy transfer results in fluorescence quenching, and the two-photon absorption ability is not high.

Method used

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  • Fluorine-perylene bisimide molecule internal-energy transferring fluorescence split compound and preparation method thereof
  • Fluorine-perylene bisimide molecule internal-energy transferring fluorescence split compound and preparation method thereof
  • Fluorine-perylene bisimide molecule internal-energy transferring fluorescence split compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment one: the preparation of fluorescent compound A:

[0029]

[0030] Fluorescent Compound A

[0031] Weigh 3.20g (5mmol) of 1,6,7,12-tetrachloro-N,N'-di-n-butyl-3,4,9,10-perylenediimide and 4.38g (12.5mmol) of bisphenol fluorene ) and 1.10 g of anhydrous potassium carbonate were added to a 500 mL three-necked flask, and then 350 mL of N-methylpyrrolidone was added. Under stirring with nitrogen, it was heated to 140°C and reacted for 6 hours. Remove from heat and cool to room temperature. The aforementioned reaction system was poured into 1000 mL of water, and the pH was adjusted to 7 with 1N HCl aqueous solution under stirring. A large amount of purple-red solid was precipitated, filtered with suction, washed twice with 95% ethanol, and dried to obtain 4.0 g of crude product. The crude product was recrystallized with chloroform to obtain 3.82 g of dark purple crystals, with a yield of 90.5%. 1 H-NMR (500MHz, CDCl 3, ppm) δ=8.631 (dd, 8H (Phen-H), J=...

Embodiment 2

[0033] Example 2: Preparation of Fluorescent Compound B

[0034]

[0035] Fluorescent Compound B

[0036] According to Example 1, 3.75 g of 1,6,7,12-tetrachloro-N,N'-di-n-octyl-3,4,9,10-perylene diimide was used instead of 1,6,7, 12-Tetrachloro-N,N'-di-n-butyl-3,4,9,10-perylenediimide. Finally, 4.08 g of dark purple crystals were obtained, with a yield of 85.5%. 1 H-NMR (500MHz, CDCl 3 , ppm) δ=8.612 (dd, 8H (Phen-H), J=8.5Hz, 2.0Hz), 8.213 (s, 4H (Per-H)), 7.738 (t, 4H (Ar-H), J= 7.5Hz), 7.360~7.342 (m, 12H (Ar-H)), 7.043 (dd, 8H (Phen-H), J=7.0Hz, 2.0Hz), 4.091 (t, 4H, J=7.5Hz), 1.238 (m, 24H), 0.845 (t, 6H, J=7.0Hz).

[0037]

Embodiment 3

[0038] Example 3: Preparation of Fluorescent Compound C

[0039]

[0040] Fluorescent compound C

[0041] According to Example 1, 4.35 g of 1,6,7,12-tetrachloro-N,N'-dodecyl-3,4,9,10-perylenediimide was used instead of 1,6, 7,12-Tetrachloro-N,N'-di-n-butyl-3,4,9,10-perylenediimide. Finally, 4.73 g of deep purple crystals were obtained, with a yield of 89%. 1 H-NMR (500MHz, CDCl 3 , ppm) δ=8.591 (dd, 8H (Phen-H), J=8.5Hz, 2.0Hz), 8.221 (s, 4H (Per-H)), 7.713 (t, 4H (Ar-H), J= 7.5Hz), 7.386~7.335 (m, 12H (Ar-H)), 7.043 (dd, 8H (Phen-H), J=7.0Hz, 2.0Hz), 4.095 (t, 4H, J=7.5Hz), 1.450~1.238 (m, 40H), 0.876 (t, 6H, J=7.0Hz).

[0042]

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Abstract

The invention relates to a fluorine-perylene bisimide molecule internal-energy transferring fluorescence split compound and a preparation method thereof. The chemical structure of the fluorescence compound is as shown in the specification, in the formula, R is branched chain alkyl, isooctyl oxy propyl or p-sulfonic acid phenyl of C4-C12. By virtue of SP3 hybridization characteristics of bisphenol fluorine 9-delta-carbon atoms, a D-pi-A system of a spiral structure is constructed, novel D-pi-A structures which are perpendicular to one another are formed, a fluorescence quenching phenomenon caused by planar pi-pi piling is blocked, the excited dipole moment, namely, the charge transferring degree inside excited molecules is improved, the frequency-doubled effect of molecules is improved, and the two-photon absorption property is remarkably improved.

Description

technical field [0001] The invention relates to a fluorene-perylene imide intramolecular energy transfer fluorescent compound and a preparation method thereof. Background technique [0002] Fluorescence resonance energy transfer refers to two different fluorophores, if the emission spectrum of one fluorophore (Donor, D) overlaps with the absorption spectrum of another fluorophore (Acceptor, A). . When the two fluorescent groups are in the same molecule, from the structural point of view, non-centrosymmetric molecules that can generate strong intramolecular charge transitions may become good nonlinear optical materials. Therefore, compounds with Donor-π-Acceptor (abbreviated as D-π-A) structure can be used as a preferred way to design and synthesize effective two-photon absorption. (I. Abota M, Belionne D, "Design of Organic Molecules with Large Two-Photon Absorption Cross Sections" [J] Science 1998 281:1653-1656. II. Belfield K D, Ren X “Near-IR Two-Photon Photoinitiate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/22
Inventor 沈卫平姜开元鲍治成于静郝婉莹
Owner SHANGHAI UNIV
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