Blue Fluorescent 4a-Aza-4b-boraphenanthrenes

Bosdet, Michael J. D.; Jaska, Cory A.; Piers, Warren E.; Sorensen, Ted S.; Parvez, Masood

doi:10.1021/ol070328y

Cited by 172 publications

(125 citation statements)

References 23 publications

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“…A theoretical prediction of strong absorption over a wide UV region for graphyne, graphdiyne, graphyne-3 B/N sheets also supports the possibility of tuning optical properties by doping with B/N. 44 Various isosteres of B/N molecules are biologically active aromatic compounds 45 and potential candidates for use in hydrogen storage, 46,47 organic electronic devices 48 and polymer electrolyte membrane fuel cells. 49 The synthesis of B-and N-doped singlewalled NTs, 50,51 B/N nanocones, B/N nanohorns 52 and their application in optoelectronic devices motivated this study.…”

Section: Introductionmentioning

confidence: 83%

Electronic and optical properties of pristine and boron–nitrogen doped graphyne nanotubes

Bhattacharya

Singh

Mondal

et al. 2015

Phys. Chem. Chem. Phys.

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First principle calculations with generalized gradient approximation were carried out to analyse the electronic and optical properties of armchair and zigzag graphyne nanotubes (GNTs). The possible application of these NTs in optoelectronic devices was also investigated. The GNTs were doped with boron (B) and nitrogen (N) atoms and the resulting band gap tuning was studied with respect to the B/N substitution site and increasing diameter of the NTs. The basis of this variation was examined using the partial density of states and crystal orbital Hamilton population analysis. A decreasing trend in the optical response was seen with an increase in the diameter of the NTs. The reported systems showed anisotropic behaviour in the low-energy region. The origin of the optical responses was monitored from the infrared to the UV region depending on the doping site of the B/N. As a result of the large band gap, low reflectivity and low refractive index, B/N GNTs have been established as a suitable system for novel optoelectronic devices. The strong absorption peaks in the UV region mean that they are a good choice for use in UV light protection.

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Section: Introductionmentioning

confidence: 83%

Electronic and optical properties of pristine and boron–nitrogen doped graphyne nanotubes

Bhattacharya

Singh

Mondal

et al. 2015

Phys. Chem. Chem. Phys.

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“…Following similar strategies, Piers and co‐workers could access a number of novel BN‐embedded PAHs (Scheme ). Reactions of boracyclohexadiene 26 with a variety of 2‐ethynylpyridines afforded the borabenzene–pyridine intermediate 27 , which underwent cyclization smoothly without any catalyst to give the phenanthrene analogue 28 with internalized BN substitution 21. The smooth cyclization of the pendent ethynyl group was attributed to the enhanced nucleophilic character of the carbon atom α to boron in the borabenzene–pyridine intermediate 27 .…”

Section: Recent Development Of Bn‐substituted Polycyclic Aromatics (Amentioning

confidence: 99%

“…For example, the fluorescence spectra of the parent phenanthrene and its two BN analogues (9,10‐azaboraphenanthrene 4 b and 4 a ‐aza‐4 b ‐boraphenanthrene 28 a ) showed extremely different emission features (Figure 3). 21 Phenanthrene exhibited emission mainly in the UV region ( λ em =347 nm) with a relatively low quantum yield ( Φ F =0.09). Replacement of the two carbon atoms at the peripheral 9,10‐positions with the BN unit resulted in a blue‐shifted emission to 327 nm, with an enhanced quantum yield ( Φ F =0.61).…”

Section: Recent Development Of Bn‐substituted Polycyclic Aromatics (Amentioning

confidence: 99%

BN Heterosuperbenzenes: Synthesis and Properties

Wang

Pei

2014

Chemistry A European J

392

149

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Replacement of C=C unit with its isoelectronic B-N unit in aromatics provides a new class of molecules with appealing properties, which have attracted great attention recently. In this Concept, we focus on BN-substituted polycyclic aromatics with fused structures, and review their synthesis, photophysical, and redox properties, as well as their applications in organic electronics. We also present challenging synthetic targets, large BN- substituted polycyclic aromatics, such as regioregular BN heterosuperbenzenes, which can be viewed as BN-doped nanographenes. Finally, we propose an atomically precise bottom-up synthesis of structurally well-defined BN-doped graphenes.

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“…[1] This class of materials allows the advantages of small molecules, such as anthracene, phenanthrene, or pyrene [2] to be combined with those of conjugated polymers, such as polyfluorenes [3] or poly(para-phenylene vinylene)s. [4] To date, the most promising design for dendrimer light-emitting-diode (DLED) materials has comprised a fluorescent [5] or a phosphorescent [6] core and a conjugated, but non-emissive, dendron shell to keep the emissive units separated, thus avoiding excimer formation and quenching effects. [1] This class of materials allows the advantages of small molecules, such as anthracene, phenanthrene, or pyrene [2] to be combined with those of conjugated polymers, such as polyfluorenes [3] or poly(para-phenylene vinylene)s. [4] To date, the most promising design for dendrimer light-emitting-diode (DLED) materials has comprised a fluorescent [5] or a phosphorescent [6] core and a conjugated, but non-emissive, dendron shell to keep the emissive units separated, thus avoiding excimer formation and quenching effects.…”

mentioning

confidence: 99%