Synthesis of π-Conjugated Polymers Containing Organoboron Benzo[<i>h</i>]quinolate in the Main Chain

Tokoro, Yuichiro; Nagai, Atsushi; Chujo, Yoshiki

doi:10.1021/ma100814v

Cited by 43 publications

(26 citation statements)

References 21 publications

(32 reference statements)

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“…[1][2][3][4][5][6][7][8][9][10] They can also be useful as dyes for medicinal purposes including bioimaging and diagnostics. [1][2][3][4][5][6][7][8][9][10] They can also be useful as dyes for medicinal purposes including bioimaging and diagnostics.…”

Section: Introductionmentioning

confidence: 99%

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

et al. 2015

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A series of diarylborinic complexes with salicydeneaniline ligands bearing various functional groups at the 6-position have been synthesized in high yields by applying a straightforward one-pot multicomponent protocol. UV-Vis measurements revealed the influence of electronic character of substituents on the observed maximum of emission (λem). This has been confirmed by a relatively strong linear correlation (R(2) = 0.92) of λem with Hammett σp(+) constants. Such a correlation was investigated using a QTAIM analysis of the charge density distribution. Absorption and emission bands for the obtained systems span between 390-437 nm and between 506-590 nm, respectively, with quantum yields reaching 17%. Time-dependent UV-Vis absorption measurements revealed that diphenylborinic salicydeneaniline complexes undergo slow degradation in solution under ambient conditions. In contrast, the use of a naphthalene-based chromophore or the introduction of fluorinated phenyl groups at the boron atom resulted in stable systems.

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Section: Introductionmentioning

confidence: 99%

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

et al. 2015

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“…The energy transfer efficiency was found to be 99.6% which explains the efficient quenching of quinolate fluorescence. This novel donor-acceptor polymeric system shows superior properties such as high fluorescence quantum yield, high energy transfer efficiency and absorption in a wide spectral range, compared with other organoboron quinolate polymers [32][33][34][35]. The fluorescence quantum yield of the polymer is also higher than other BODIPY based conjugated polymers [10,[27][28][29].…”

Section: Photophysical Propertiesmentioning

confidence: 91%

“…Organoboron quinolates and their conjugated polymers have received significant attention due to their potential applications in organic light-emitting diodes (OLEDs) [1,32,35]. In all known organoboron quinolate polymers, the quinolate ligand is the acceptor while the aromatic π-conjugated main chain is the donor [32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

“…In all known organoboron quinolate polymers, the quinolate ligand is the acceptor while the aromatic π-conjugated main chain is the donor [32][33][34][35]. Because quinolates absorb and emit at higher energy in comparison with BODIPY, we reasoned that a co-polymer of an organoboron quinolate and E-BODIPY would produce a new polymer where quinolate is the donor and the E-BODIPY is the acceptor.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units

2012

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KEYWORDSA novel fluorescent co-polymer with an organoboron quinolate and an E-BODIPY (BODIPY: 4,4-difluoro-4-bora-3a-4a-diaza-s-indacene) moiety was synthesized with the aim of producing a donor-acceptor polymeric system where the organoboron quinolate acts as the donor and the E-BODIPY moiety is the acceptor. The polymer has three prominent absorption bands: 264 nm (corresponding to the organoboron quinolate), 397 nm (corresponding to the organoboron quinolate and BODIPY) and 516 nm (corresponding to the E-BODIPY moiety). Excitation of the organoboron quinolate at 264 nm resulted in emission at 525 nm, giving a 261 nm Stokes shift. Energy transfer from the donor (organoboron quinolate) unit to the acceptor (BODIPY) explains the origin of this large Stokes shift.

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“…The peak at 345 nm of compound 5 was blue shifted (by 35 nm) to 311 nm and its absorbance value increased. In addition, the appearance of a broad band around 430e440 nm indicated the formation of the proposed boronate ester of the Schiff base with a phthalonitrile group [53,54] (Fig. 1).…”

Section: Uvevis Spectra Of Compounds 2 3 5 Andmentioning

confidence: 99%

Boronic ester of a phthalocyanine precursor with a salicylaldimino moiety

Özçelik¹,

Gül²

2012

Journal of Organometallic Chemistry

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Synthesis of π-Conjugated Polymers Containing Organoboron Benzo[h]quinolate in the Main Chain

Cited by 43 publications

References 21 publications

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

Tuning of the colour and chemical stability of model boranils: a strong effect of structural modifications

Synthesis of an E-BODIPY based fluorescent Co-polymer containing organoboron quinolate units

Boronic ester of a phthalocyanine precursor with a salicylaldimino moiety

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