Organoboron compounds. Part VIII. Aliphatic and aromatic diboronic acids

Coutts, I. G. C.; Goldschmid, H. R.; Musgrave, O. C.

doi:10.1039/j39700000488

Cited by 69 publications

(72 citation statements)

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“…Thus, condensation of 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP) with 2,5-thiophenediboronic acid (H 4 TDB) (21) in dioxane and mesitylene at 120°C over 72 h afforded (HOTP) 2 (TDB) 3 (T-COF 1; HOTP = 2,3,6,7,10,11-hexaoxytriphenylene) as an off-white powder. Boronate ester linkages were confirmed by fourier transform infrared spectroscopy (FT-IR) spectroscopy, which revealed stretching frequencies at 1,348, 1,323, and 1,225 cm…”

Section: Resultsmentioning

confidence: 99%

Thiophene-based covalent organic frameworks

Bertrand

Michaelis

Ong

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

304

205

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We report the synthesis and characterization of covalent organic frameworks (COFs) incorporating thiophene-based building blocks. We show that these are amenable to reticular synthesis, and that bent ditopic monomers, such as 2,5-thiophenediboronic acid, are defect-prone building blocks that are susceptible to synthetic variations during COF synthesis. The synthesis and characterization of an unusual charge transfer complex between thieno[3,2-b]thiophene-2,5-diboronic acid and tetracyanoquinodimethane enabled by the unique COF architecture is also presented. Together, these results delineate important synthetic advances toward the implementation of COFs in electronic devices.electronic materials | polymers | porous materials C ovalent organic frameworks (COFs) have emerged as an important class of polymeric crystalline materials with potential applications that complement those of metal organic frameworks (MOFs) (1-7). In particular, 2D COFs exhibit unique architectures wherein the monomers that make up their 2D layers stack almost perfectly into infinite 1D columns that are ideal for charge and exciton transport (6-12). Such electronic properties are particularly difficult to engineer in microporous MOFs, where high charge mobility and conductivity have only recently been demonstrated (13-15). Despite their layered structures, the typical hexagonal or square lattices of 2D COFs exhibit large 1D channels with well-defined pores that can be subject to reticular chemistry and postsynthetic modification (16,17), and where complementary donor or acceptor molecules may in principle be inserted. Clearly, the unprecedented combination of high surface area, crystallinity, chemical and pore size tunability, and unique molecular architecture make COFs tantalizing targets for a new generation of electronic devices, including sustainable batteries, field-effect transistors, and photovoltaics. The first steps toward such applications must involve the incorporation of electroactive monomers within the COFs. This has been beautifully exemplified by the insertion of porphyrins (18), phthalocyanines (9), pyrene (8), naphthalenetetracarboxydiimide (19), and benzothiadiazole (20) in such materials. Notably, however, one of the most popular monomers in conductive organic polymers, thiophene, has not been incorporated in COFs thus far. Herein, we report the synthesis and characterization of thiophene-based COFs, including materials made from thiophene-, bithiophene-, and thienothiophene-diboronic acids. We also advance a hypothesis regarding the more general synthetic tractability of COFs made from bent ligands. Finally, we show that p-type COFs are amenable to doping with electron acceptors and report an unusual charge-transfer complex with tetracyanoquinodimethane (TCNQ). Results and DiscussionWe prepared thiophene-based COF (T-COFs) under conditions mimicking those used for the synthesis of the prototypical COF-5. Thus, condensation of 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP) with 2,5-thiophenediboronic acid (H 4 TDB) (21) in...

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Section: Resultsmentioning

confidence: 99%

Thiophene-based covalent organic frameworks

Bertrand

Michaelis

Ong

et al. 2013

Proc. Natl. Acad. Sci. U.S.A.

304

205

View full text Add to dashboard Cite

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“…IH NMR spectrum [bin CDC1 3 ] showed signals at 1.35 (t, 3H, J =7 Hz), 1.37 (t, 3H, J = Hz), 4.35 (q, 2H, J = 7 Hz), 4.37 (q, 2 H, J = 7 Hz), 7.59-7.67 (m, 2H), and 7.82 (d, lH, J = 2.2 Hz). 13 15.46 g (48 mmol) ofll, 36.1 g (120 mmol) ofl, potassium carbonate (16.58 g, 120 mmol), and 100 mL of deoxygenated N, N -dimethylformamide were added to a flask equipped with a reflux condenser. The flask was flushed with nitrogen, and 1.5 g tetrakis(triphenlphosphine)paladium (Pd(PPh 3 ) 4 were added to the reaction mixture.…”

Section: Monomer Synthesismentioning

confidence: 99%

Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''',4,4'''-p-Quarterphenyltetracarboxylic Dianhydride

Morikawa

2000

Polym J

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ABSTRACT:A new rigid tetracarboxylic dianhydride, 3,3"',4,4"' -p-quarterphenyltetracarboxylic dianhydrjde, was synthesized in three steps starting from diethyl 4-bromophthalate. New aromatic polyimides containing a p-quarterphenyl unit were synthesized from this tetracarboxylic dianhydride and various aromatic diamines by the conventional two-step procedure that included ring-opening polyaddition in a polar amide-type solvent and subsequent thermal cyclic dehydration. These polyimides had inherent viscosities of 0.41-0.83 dl g-1, and were insoluble in organic solvents.The glass transition temperatures (Tg) of the polyimides were 220-260°(, and exothermic crystallization was observed on heating above its Tg. Almost all the polyimides underwent melting prior to its decomposition.

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“…N-methyl-2-pyrrolidone (NMP) was purified by vacuum distillation over calcium hydride. Diethyl 4-bromophthalate (1), 12 (4-methoxyphenyl)boronic acid (11), 13 and bis(trimethylene)-4,4'-biphenylenediboronate (VII) 14 were prepared as previously reported.…”

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confidence: 99%

Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''''',4,4'''''-p-Sexiphenyltetracarboxylic Dianhydride

Morikawa

Hosoya

2000

Polym J

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ABSTRACT:A new rigid tetracarboxylic dianhydride, 3,3"'", 4,4"'"-p-sexiphenyltetracarboxylic dianhydride, was synthesized in seven steps starting from diethyl 4-bromophthalate. New aromatic polyimides containing a p-sexiphenyl unit were synthesized from this tetracarboxylic dianhydride and various aromatic diamines by the conventional twostep procedure of ring-opening polyaddition in a polar amide-type solvent and subsequent thermal cyclic dehydration. These polyimides had inherent viscosities of 1.20-1.69 dL g-1 , and were insoluble in organic solvents. The polyimides were characterized by differential scanning calorimetry (DSC), thermogravimetry (TG), wide-angle X-Ray diffraction measurements, and dynamic mechanical analysis (DMA). Typical polyimides were noncrystalline and showed excellent thermal stability, and had glass transition temperatures (Tg) at about 250'C. Decrease in the modulus at the glass transition temperature was less than corresponding polyimides having no p-sexiphenyl unit due to the presence of the rigid p-sexiphenyl unit.

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Organoboron compounds. Part VIII. Aliphatic and aromatic diboronic acids

Cited by 69 publications

References 0 publications

Thiophene-based covalent organic frameworks

Thiophene-based covalent organic frameworks

Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''',4,4'''-p-Quarterphenyltetracarboxylic Dianhydride

Synthesis and Characterization of Novel Aromatic Polyimides from Aromatic Diamine and 3,3''''',4,4'''''-p-Sexiphenyltetracarboxylic Dianhydride

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