Synthesis of organoaluminum polymers with aluminum – nitrogen ring in their main-chain

Nagata, Yuuya; Chujo, Yoshiki

doi:10.1080/10241220701650915

Cited by 1 publication

(3 citation statements)

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“…The chiral borane monomer, N,N,N′,N′ -tetramethylethylenediamine-bis(monoisopinocampheylborane) ( S -IpcBH 2 ·TMED), as S -alpine−boramine is currently commercially available. The polymers were prepared by the hydroboration polycondensations of three aromatic dicyano compounds, 1,4-dicyanobenzene ( 1a ), 1,3-dicyanobenzene ( 1b ), and 1,4-didodecyloxy-2,5-dicyanobenzene ( 1c ), using S -IpcBH 2 ·TMED in diglyme (2.5 mol/L) at 100 °C at [M]/[S-IpcBH 2 ·TMED] = 1 for 24 h (Scheme ). After polymerization, the polymers were precipitated in methanol and collected under air and moisture in 61−76% yields.…”

Section: Resultsmentioning

confidence: 99%

“…1,4-Didodecyloxy-2,5-dicyanobenzene was prepared according to the reported procedure. 21 Hydroboration Polycondensation of 1,4-Dicyanobenzene with S-Alpine-Boramine (2a). Typical Procedure.…”

Section: Methodsmentioning

confidence: 99%

“…1,4-Dicyanobenzene (Wako Chemical, Co., 98%) and 1,3-dicyanobenzene (Wako Chemical, Co., 98%), S -alpine−boramine ( S -IpcBH 2 ·TMED) (Aldrich Chemical, Co.), R -alpine−boramine ( R -IpcBH 2 ·TMED) (Aldrich Chemical, Co.), and bis[2-(2-methoxyethoxy)ethyl] ether (diglyme) (Wako Chemical, Co., 95%) were used as received. 1,4-Didodecyloxy-2,5-dicyanobenzene was prepared according to the reported procedure …”

Section: Methodsmentioning

confidence: 99%

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A Facile Synthesis of Chiral Luminescent Organoboron Polymers by Hydroboration Polymerization Utilizing Chiral Borane

et al. 2009

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Hydroboration polycondensations of three aromatic dicyano compounds 1, 1,4-dicyanobenzene (1a), 1,3-dicyanobenzene (1b), and 1,4-didodecyloxy-2,5-dicyanobenzene (1c), with N,N,N′,N′-tetramethylethylenediamine-bis(monoisopinocampheylborane) (S-IpcBH2·TMED) were carried out to obtain optically active poly(cyclodiborazane)s (2a, 2b, and 2c) with M ns in the range from 2400 to 6800 in 61−76% yields. The hydroboration polycondensation efficiently proceeded through the complete formation of boron−nitrogen four-membered ring. The polymer structures were characterized by 1H and 11B NMR, UV−vis, photoluminescence (PL), and CD spectroscopies. Only 2c exhibited intense blue-green light emission from charge-transfer interaction by incorporation of donor and acceptor system into the polymer backbone. The emission behavior of model compounds (A and B), corresponding to polymer units of 2a and 2c, was effectively examined by theoretical calculations using the DFT method. As a result, the intense blue-green emission of 2c was observed by the bathochromic shift to a visible region. All the polymers showed intense CD signals, indicating that they formed chiral boron−nitrogen four-membered ring structure. Further, 3b and 3c were prepared by hydroboration polycondensation of 1b or 1c with R-IpcBH2·TMED. The specific rotations of 2a, 2b, and 2c showed positive values in contrast to those of 3b and 3c. The Cotton effects of the cyanobenzene moieties in 2a, 2b, and 2c at around 300−350 nm were positive, whereas the Cotton effects of the cyanobenzene moieties in 3b and 3c were negative, as were the specific rotations as well.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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