Aromatic and aromatic/heteroaromatic molecular structures with controllable electron conducting properties

a molecular structure and electron conducting technology, applied in the direction of non-metal conductors, conductors, transportation and packaging, etc., can solve the problems of difficult connection of conductive molecules to electrodes, difficult conductivity measurement of single molecules, and difficulty in discovering new conductive molecules

Inactive Publication Date: 2011-02-03
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the discovery of new conductive molecules for this is fraught with difficulty.
Additionally, it is difficult to connect conductive molecules to electrodes and even more difficult to perform conductivity measurements on single molecules.
In addition to the difficulties in construction, the design of new molecules possessing useful properties is hampered by the lack of a facile method for correlating the effects of optical transitions to electronic molecular properties.
Once a structure is designed, the synthesis, purification and growth of single crystals of molecules as large as these is not easily accomplished.
Finally, the coupling of different aromatic and heteroaromatic building blocks is difficult to achieve because substituted structures are prone to side reactions and long reaction times.
The above listed references teach the synthesis of useful compounds, however do not address the need for functionalized molecules specifically adapted for facile nano-device fabrication.

Method used

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  • Aromatic and aromatic/heteroaromatic molecular structures with controllable electron conducting properties
  • Aromatic and aromatic/heteroaromatic molecular structures with controllable electron conducting properties
  • Aromatic and aromatic/heteroaromatic molecular structures with controllable electron conducting properties

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 1,4-Bis(4-Pyridyl)Butadiyne)

Reagents Used Include:

[0055]4-Ethynylpyridine hydrochloride: 97%, Mw=139.58, Mp 150° C., Aldrich: 53,092-1[0056]Diethyl Ether: Mw=74.12 d=0.713, Bp 35-36° C.[0057]Triethylamine: Mw=101.19 d=0.726, Mp −115° C., Bp 88.8° C., Aldrich: 47,128-3[0058]Copper (I) Chloride: Mw −98.99, Mp 430° C., Aldrich: 22, 962-8[0059]Oxygen: Mw=32, Mp −218° C., Bp −183° C., Aldrich: 29,560-4[0060]4-Ethynylpyridine: Mw=103.1237, Mp 95-96° C.,[0061]Pyridine: Mw=79.10, D=0.983, Bp 115-115° C. Aldrich: 27,097-0

[0062]This compound was synthesized by oxidative coupling of 4-ethynyl pyridine (freshly prepared from its hydrochloride form as described below) in pyridine in the presence of copper (I) chloride according to the following reaction scheme:

[0063]Crystallization from carbon tetrachloride gave colorless plates with the following structure as determined from X-ray diffraction data.

[0064]Crystal Data: C14H8N2, from carbon tetrachloride, colorless, irregular plate,...

example 2

Preparation of 4-Ethynyl(Pyridine)-4′-Ethynylphenyl-5′-Nitro-1-Pyridine

[0068]

This compound was synthesized as described above in Example 1. Crystallization from ethanol gave colorless needles with the following structure as determined from X-ray diffraction data. It can be seen that the mean plane of the outer rings forms an angle of 28.3 degrees with the inner ring.

[0069]Crystal Data: C20H11N3O2, from ethanol, colorless, needle, ˜0.220×0.020×0.020 mm, monoclinic, C2 / c, a=16.351(3) Å, b=11.659(3) Å, c=9.2685(19) Å, beta=117.706(5)°, Vol.=1564.3(6) Å3, Z=4, T=−100° C., Formula weight=325.32, Density=1.381 mg / m3, μ(Mo)=0.09 mm−1.

example 3

Preparation of 4-Ethynyl(Pyridine)-4′-EthynylBiphenylene-1-Pyridine

[0070]

[0071]4-Ethynyl(pyridine)-4′-ethynylbiphenylene-1-pyridine can be synthesized according to the procedure outlined in Example 1 via the reaction scheme shown above.

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Abstract

Aromatic and aromatic / heteroaromatic molecular structures with controllable electron conducting properties are derived from the incorporation of electron active substituents in selective positions.

Description

[0001]This application claims the benefit of U.S. Utility patent application Ser. Nos. 10 / 722,304 filed Nov. 25, 2003, and 11 / 511,934 filed Aug. 28, 2006.FIELD OF INVENTION[0002]The invention is directed to the preparation of novel aromatic and aromatic / heteroaromatic molecular structures with controllable electron conducting properties which can form self-assembled layers on metal or other substrates, and can be used in molecular scaled electronic devices.BACKGROUND[0003]The expanding commercial interest in the generation of small nano-scale electronic devices highlights a need for the generation of a new class of conductive molecules that are functionalized for use in nano-electronic device fabrication. However, the discovery of new conductive molecules for this is fraught with difficulty. For example, little is known about the specifics of how conductive molecules work. Additionally, it is difficult to connect conductive molecules to electrodes and even more difficult to perform ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H01B1/12C07D401/06C07D401/10C07C255/51C07C381/00C07C255/50C07C25/13C07D401/14B05D1/12C07C25/24C07C327/22C07D213/16C07D215/12C07D271/10C07D271/107
CPCC07C25/24C07C255/50C07C255/51C07C327/22C07D215/12C07D271/107C07C2603/50C07D213/06Y10T428/31971Y10T428/31645
Inventor FRENCH, ROGER HARQUAILGETTY, ROSSPERCEC, SIMONA
Owner EI DU PONT DE NEMOURS & CO
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