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Covalent organic frameworks and methods of making same

A technology of covalent organic framework and crystalline state, applied in the direction of organic chemistry, chemical instruments and methods, and other chemical processes, can solve the problem of no COF

Inactive Publication Date: 2013-02-13
CORNELL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the initial activity, no new boronate-linked COFs have been reported

Method used

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  • Covalent organic frameworks and methods of making same
  • Covalent organic frameworks and methods of making same
  • Covalent organic frameworks and methods of making same

Examples

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Embodiment 1

[0090] This example describes a general method for the synthesis of boronic ester-linked COFs that avoids the direct use of insoluble and unstable multifunctional catechol reactants. Using the described method, two-dimensional networks of coplanar stacked phthalocyanines (Pcs), which are strongly absorbing chromophores, have been prepared in bulk heterojunction / dye-sensitized solar cells, as well as for many other applications . The phthalocyanine COFs form overlapping two-dimensional square lattices as determined by powder X-ray diffraction, surface area analysis, and ultraviolet / visible / near-infrared and fluorescence spectroscopy. The materials can be used to form COF-based bulk heterojunctions characterized by structurally precise and high surface area interfaces between complementary organic semiconductors.

[0091] The direct formation of boronate esters from protected catechols provides an attractive option for the synthesis of COFs, since the protecting group can reduc...

Embodiment 2

[0146] Example of COF

[0147] The structure of the COF in this embodiment is as follows Figure 32 shown.

[0148] ZnPc-PDBA COF. Pyrene diboronic acid 1 (17mg, 0.059mmol) and zinc octylhydroxyphthalocyanine 5 (20mg, 0.028mmol) (see Figure 33 ) in a mixture of dioxane and methanol (2:1, 3 mL) and sonicated for 10 min. The dark green suspension was transferred to a 10 mL scored long-neck glass ampoule, snap-frozen in a liquid nitrogen bath, and flame-sealed. The ampoule was placed in a gravity convection oven at 120°C for 96 hours, and the resulting free-flowing dark green powder was collected by filtration through a Hershey funnel, washed with 1 mL of anhydrous toluene, and air-dried. After brief vacuum drying, PXRD and IR characterizations were performed immediately. ZnPc-PDBA COF 10 mg (52%) was isolated. IR (powder, ATR) 3233, 1607, 1459, 1369, 1337, 1271, 1231, 1106, 1078, 1023, 902, 870, 824, 742, 714cm -1 . PXRD [2θ (relative intensity)] 3.22 (100), 6.50 (24), 9...

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Abstract

Crystalline COFs comprising a phthalocyanine moiety and a boron-containing multifunctional linking group joined by boronate ester bonds. A method for making crystalline COFs comprising Lewis acid catalyzed formation of boronate ester bonds between protected catechol subunits and multifunctional linkers comprising boronic acid groups. The COFs can be used in applications such as, for example, electronic devices.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Patent Application 61 / 321,649, filed April 7, 2010, the contents of which are hereby incorporated by reference. [0003] Statement Regarding Federally Funded Research [0004] This invention was made with government support under National Science Foundation grants CHE-0847926 and CHE-0936988. The US Government has certain rights in this invention. technical field [0005] The present invention generally relates to covalent organic frameworks, methods of making the frameworks, uses of the frameworks, materials comprising the frameworks, and devices comprising the frameworks. Background technique [0006] Continued development of organic semiconductors will lead to flexible displays, radio frequency identification (RFID) tags, improved lighting technologies, efficient sensors, and economically competitive solar cells. Apart from their low cost, one of the most attract...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07D487/22H01L31/042H01L51/00B01J20/22H10K99/00
CPCB01J20/22H01L51/0078B01J20/28057H01L51/009B01J20/226B01J20/28004C07F5/025Y02E10/549H10K85/311H10K85/361H10K85/381
Inventor W·R·迪奇特尔E·L·斯皮特莱尔
Owner CORNELL UNIVERSITY
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