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Synthesis of poly-(p-aryleneethynylene)s in neat water under aerobic condit

a technology of arylene and ethylene, which is applied in the field of polymer synthesis, can solve the problems of inability to implement in the presence of water, inability to synthesize carbyne precursors for adimet protocols, and inability to achieve inert reaction conditions

Inactive Publication Date: 2009-12-31
THE TRUSTEES OF THE UNIV OF PENNSYLVANIA
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Problems solved by technology

While the Sonogashira reaction is compatible with polar functional groups and water, it requires both dihaloarene and diethynylarene synthons, and is accordingly susceptible to the introduction of butadiyne defects in the PPE polymer, which defects are estimated to range from 1 to 10% even under the carefully controlled reaction conditions.
An ADIMET-based synthesis may circumvent butadiyne defect sites, but this method is generally incompatible with sensitive functional groups that include water-soluble side chains; furthermore, the syntheses of carbyne precursors for ADIMET protocols require inert reaction conditions and cannot be implemented in the presence of water.

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  • Synthesis of poly-(p-aryleneethynylene)s in neat water under aerobic condit
  • Synthesis of poly-(p-aryleneethynylene)s in neat water under aerobic condit
  • Synthesis of poly-(p-aryleneethynylene)s in neat water under aerobic condit

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[0100]Certain reactions involving alkynylboranes, alkynylboronic acid or alkynylborate derivatives, and alkynyltrifluoroborates are accepted. Reactions involving reagents that possess boron functionality at the 1- and 2-carbon positions of ethyne, however, have not yet been reported. This motivated the synthesis of [1,2-bis(4′,4′,5′,5′-tetramethyl[1′,3′,2′]dioxaborolan-2′-yl)ethyne (B2C2). The 1H NMR spectrum of B2C2 is shown in FIG. 1. FIG. 2 depicts the 13C NMR spectrum of B2C2 in C6D6, and FIG. 3 depicts the 11B NMR spectrum of B2C2 in C6D6.

[0101]Reaction of dilithioacetylide with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, followed by treatment with anhydrous HCl, cleanly afforded B2C2 in high yield (Scheme 1). B2C2 was recrystallized from hexanes, giving a robust crystalline solid (mp=270° C.) that is stable under ambient atmosphere for at least 1 year. B2C2 exhibited high solubility in basic water and virtually all organic solvents.

[0102]X-ray quality crystals of B2C...

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Abstract

Provided are ethyne synthons comprising boron and related methods. Also provided are related water-soluble arylethynylene polymers capable of being synthesized in neat water under aerobic conditions.

Description

RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Application 61 / 031,831, filed on Feb. 27, 2008, the entirety of which is incorporated by reference herein.STATEMENT OF GOVERNMENT INTEREST[0002]The government may have certain rights in this invention. This work was supported by a grant from the Division of Chemical Sciences, Office of Basic Energy Research, U.S. Department of Energy (DE-FGO2-02ER15299). Additional support was provided by MRSEC (DMR-00-79909) and NSEC (DMR-0425780) Programs of the National Science Foundation.FIELD OF THE INVENTION[0003]The present invention relates to the field of polymer chemistry. The present invention also relates to the field of polymer synthesis.BACKGROUND OF THE INVENTION[0004]Ethyne-bridged conjugated polymers impact a wide-range of technologies. The efficacy of these species derives not only from their established semiconducting and optical properties but also from the facts that these rigid, rod-like structures are readil...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G83/00
CPCC08G61/02C08G61/124C08G2261/1424C08G2261/411C08G2261/314C08G2261/3328C08G2261/1452
Inventor KANG, YOUN K.DERIA, PRAVASTHERIEN, MICHAEL J.
Owner THE TRUSTEES OF THE UNIV OF PENNSYLVANIA
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