Towards crystal engineering of solid-state polymerization in dibromothiophenes

Lepeltier, Marc; Hiltz, Jonathan; Lockwood, Tobias; Bélanger‐Gariépy, Francine; Perepichka, Dmitrii F.

doi:10.1039/b822997j

Cited by 36 publications

(30 citation statements)

References 38 publications

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“…Thus, its effective halogen distance (Br/Br) value is 5.634 Å, which is longer 52.3% than double van der Waals radius (2 r w ) of bromine. It is noted that this distance is quite long among reported thiophene monomers crystals . In addition, it is accepted that atomic movements within crystals were restricted to <4.2 Å distances in those organic solid reactions .…”

Section: Resultsmentioning

confidence: 97%

“…28 Recently, we had proposed a powerful strategy through thiophene molecular parallel design and successfully developed a platform of EDOT-CH(R)-EDOT 29,30 for C-C bulk polycondensation. It is worth noting that all monomers developed so far have EDOT or its analogs, [9][10][11][29][30][31][32][33][34][35][36][37] which would restrict its further modification or application because of the difficulty of functionization on EDOT or on its analogs building blocks. Generally, conjugated poly(bis-thiophene methine)s [38][39][40][41][42] derivatives are frequently synthesized through acid-catalyzed polycondensation of thiophen derivatives with aromatic aldehydes and electrochemical polymerization of bis[2-(3,4-ethylenedioxy)thienyl]methine in solution phase.…”

Section: Introductionmentioning

confidence: 99%

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Functionalization of poly(bis‐thiophene methine)s via facile C–C bulk polymerization and their application as chemosensors for acid detection

Peng

Pei

Huang

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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Up to now, 3,4‐ethylenedioxythiophene (EDOT) or its modified analogs are indispensable units or subunits in all successful monomers for polythiophene synthesis through solid‐state polymerization (SSP). Here, a more open thiophene‐(CH(R))‐thiophene platform was developed successfully and corresponding poly(bis‐thiophene methine)s were obtained via C–C SSP or melt‐state polymerization (MSP), that is, bulk polymerization. Meanwhile, the observation of quite long effective Br–Br distance of 5.634 Å, which is more than 50% of halogen's double van der Waals radius (2rw), would help us to understand powerful capability of modulation of molecule movement and reaction under SSP. In addition, these polymers were further employed as acid sensors and they show highly sensitive response to HCl, MeSO3H, BF3‐OEt2, and HNO3. The detailed experiment reveals that P1 has the detection limit of 3.35 × 10−5 M for HCl. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1676–1683

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Functionalization of poly(bis‐thiophene methine)s via facile C–C bulk polymerization and their application as chemosensors for acid detection

Peng

Pei

Huang

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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“…Recently, solid‐state polymerization of 2,5‐dihalothiophene derivatives under solventless and catalyst‐free conditions has attracted significant attention for the synthesis of highly ordered polymers and macroscopic polymer single crystals 14, 63–65. In 2003, Skabara and coworkers demonstrated the applicability of this method for the preparation of bromine‐doped PEDTT by heating the crystal of DBEDTT 14.…”

Section: Resultsmentioning

confidence: 99%

Effectiveness of alternating mammography and magnetic resonance imaging for screening women with deleterious BRCA mutations at high risk of breast cancer

Le‐Petross

Whitman

Atchley

et al. 2011

Cancer

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BACKGROUND: Magnetic resonance imaging (MRI) has been used to supplement screening mammography and clinical breast examination (CBE) in women who are at high risk of developing breast cancer. In this study, the authors investigated the efficacy of alternating screening mammography and breast MRI every 6 months in women who had a genetically high risk of developing breast cancer. METHODS: A retrospective chart review was performed on all women who were seen in a high-risk breast cancer clinic from 1997 to 2009. Patients with breast cancer gene (BRCA) mutations who underwent alternating screening mammography and breast MRI every 6 months were included in the study. Mammography, ultrasonography, MRI, and biopsy results were reviewed. RESULTS: Of 73 patients who met the study criteria, 37 had BRCA1 mutations, and 36 had BRCA2 mutations. Twenty-one patients (29%) completed 1 cycle of mammography and MRI surveillance, 23 patients (31%) completed 2 cycles, 18 patients (25%) completed 3 cycles, and patients 11 (15%) completed !4 cycles. The median follow-up was 2 years (range, 1-6 years). Thirteen cancers were detected among 11 women (15%). The mean tumor size was 14 mm (range, 1-30 mm), and 2 patients had bilateral cancers. Twelve of 13 cancers were detected on an MRI but not on the screening mammography study that was obtained 6 months earlier. One cancer (a 1-mm focus of ductal carcinoma in situ) was an incidental finding in a prophylactic mastectomy specimen. One patient had ipsilateral axillary lymphadenopathy identified on ultrasonography but had no evidence of lymph node involvement after neoadjuvant chemotherapy and surgery. CONCLUSIONS: In women who were at genetically high risk of developing breast cancer, MRI detected cancers that were not identified on mammography 6 months earlier. Future prospective studies are needed to evaluate the benefits of this screening regimen.

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“…22 The compound represents one of the closest relatives to EDOT, in which its corresponding polymer could behave similarly to PEDOT with potentially better processing property due to larger hydrocarbon portion. 11,13 Surface morphologies of the monomer DB1 and polymer P1 were compared to follow the transformation process during the SSP. The product was then brominated by NBS to obtain the precursor DB1 in excellent yield.…”

Section: Resultsmentioning

confidence: 99%

“…[11][12][13][14][15][16][17] Nevertheless, this fascinating procedure still found some limitations. [11][12][13][14][15][16][17] Nevertheless, this fascinating procedure still found some limitations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of functionalizable derivatives of 3,4‐ethylenedioxythiophene and their solid‐state polymerizations

Gulprasertrat

Chapromma

Aree

et al. 2015

J of Applied Polymer Sci

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Four polythiophenes based on poly(3,4-ethylenedioxythiophene) (PEDOT) framework have been successfully prepared by the facile thermal activated solid-state polymerization (SSP) process from their corresponding dibromothiophene derivatives, which were efficiently obtained using our improved methodology. Rates of polymerizations of these precursors were varied and most of the processes were incomplete under the reaction condition chosen for the synthesis. Raising the reaction temperature of the SSP further advanced the polymerization progress and improved the conductive properties of the polymer. The polymer of 3,4-ethylenedioxythiophene-methanol (EDTM) and its two related derivatives with functionalizable groups were prepared for the first time by the SSP method. The process and these new SSP-derived polymers could help solving the fabrication difficulty and expand the scope of their applications.

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Towards crystal engineering of solid-state polymerization in dibromothiophenes

Cited by 36 publications

References 38 publications

Functionalization of poly(bis‐thiophene methine)s via facile C–C bulk polymerization and their application as chemosensors for acid detection

Functionalization of poly(bis‐thiophene methine)s via facile C–C bulk polymerization and their application as chemosensors for acid detection

Effectiveness of alternating mammography and magnetic resonance imaging for screening women with deleterious BRCA mutations at high risk of breast cancer

Synthesis of functionalizable derivatives of 3,4‐ethylenedioxythiophene and their solid‐state polymerizations

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