Doping Polycyclic Arenes with Nitrogen–Boron–Nitrogen (NBN) Units

Yang, Deng‐Tao; Nakamura, Tomoya; He, Zhechang; Wang, Xiang; Wakamiya, Atsushi; Peng, Tai; Wang, Suning

doi:10.1021/acs.orglett.8b02850

Cited by 84 publications

(76 citation statements)

References 32 publications

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“…These T-shaped luminogens exhibit good absolutef luorescenceq uantumy ields of up to 0.62 in the case of NBN-TPA,w hich is comparablet ot he values of the reported NBN-embedded small molecules. [9][10][11][12] However, NBN-An only offered an extremelyl ow fluorescenceq uantum yield of 0.04, likely associatedw ith the free rotation of the anthraceneg roup, which is in good agreement with it having the broadest emission spectra among the five NBN-DBP-Fns.…”

Section: Resultssupporting

confidence: 52%

“…In particular, such NBN-embedded dibenzophenalenec ores can be facilely brominated at their N-para positions,t hus allowing for further modifications,s uch as the introduction of various aryl units by transition-metal-catalyzed cross-couplingr eactions to achieve p-extended oligomers. On the other hand, Wang et al [10] and Feng et al [11] successfully fused the backboneso fNBN-DBP with other aromatic rings (Figure 1a and b). The resulting NBN-phenalene cored PAHi n Figure1bwas used to fabricate organic field transistor devices, exhibiting good electron carrierm obility,i ndicative of its extended p-conjugation.…”

Section: Introductionmentioning

confidence: 99%

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Concise Approach to T‐Shaped NBN‐Phenalene Cored Luminogens as Intensive Blue Light Emitters

Sun

Ding

Qiang

et al. 2020

Chemistry A European J

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Small organic molecules with finely tunable physical properties are highlyd esired for the fabricationo fl owcost and high-performance organic electronic devices.Int his work, the syntheses of as eries of T-shaped NBN-embedded dibenzophenalene derivatives throught he formationo fa key brominated intermediate in as toichiometrically controlled reactiona re presented. The geometrica nd electronic structures of these T-shaped molecules can be simply tailored by attaching substituents along the direction perpendicular to the molecular main backbones,r esulting in desirable physical properties, such as high thermals tability with a decomposition temperature of more than 350 8C, and intensive blue luminescence with aq uantum yield up to 0.62. Organic light-emitting diode devices fabricated with such moleculesa st he emittingl ayer release pure blue light with CIE (0.16,0 .12).

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Section: Resultssupporting

confidence: 52%

Section: Introductionmentioning

confidence: 99%

Concise Approach to T‐Shaped NBN‐Phenalene Cored Luminogens as Intensive Blue Light Emitters

Sun

Ding

Qiang

et al. 2020

Chemistry A European J

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“…The polycyclic arene 188 doped with a nitrogen‐boron‐nitrogen unit has been synthesized by using DDQ in the presence of triflic acid to efficiently close the seven‐membered ring (Figure ) …”

Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

“…[196] Thep olycyclica rene 188 doped with an itrogen-boronnitrogen unit has been synthesized by using DDQ in the presence of triflic acid to efficiently close the seven-membered ring (Figure 14). [197] Many p-extended porphyrins have been synthesized by inter-o ri ntramolecular oxidative coupling;h owever, they will not be described here due to space restrictions and the fact that this subject has been reviewed recently. [198,199] As reported by Tanaka, Kim, Osuka, and co-workers, similar to porphyrin analogues, meso-meso-linked corrole dimers 189 a-c bearing various aryl substituents can also be oxidatively planarized to the corresponding triply linked products 190 a-c (Scheme 28).…”

Section: Dyes and Heterocyclic Polyarenesmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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“…[17][18][19] Noticeable examples include BN-doped pyrenes, [16] phenanthrenes, [20] anthracenes, [21] perylenes [22,23] and nanographenes. [9,[24][25][26] In these PAHs, the doping units are isolated BN couples selectively placede ither at the peripheries or in the core of aromatic precursors bearing amino groups at specific positions. Another strategy consists in the use of preorganized dopingu nits, in which the BN and BO couples are clustered in six-membered rings and used to replace benzenoid rings.…”

Section: Introductionmentioning

confidence: 99%

Boron–Nitrogen‐Doped Nanographenes: A Synthetic Tale from Borazine Precursors

Dosso

Battisti

Ward

et al. 2020

Chemistry A European J

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In this work, ac omprehensive account of the authors' synthetic efforts to prepareb orazino-doped hexabenzocoronenes by using the Friedel-Crafts-type electrophilic aromatic substitution is reported. Hexafluoro-functionalized aryl borazines, bearing an ortho fluoride leaving group on each of the N-and B-aryl rings,w as shown to lead to cascade-type electrophilica romatic substitution events in the stepwise CÀCbond formation, giving higher yields of borazinocoronenes than those obtained with borazine precursors bearing fluoride leavingg roups at the ortho positions of the B-aryl substituents. By using this pathway,a nu nprecedented boroxadizine-doped PAHf eaturing ag ulf-type periphery could be isolated,a nd itss tructure proven by single-crystal X-ray diffraction analysis. Mechanistic studies on the stepwise Friedel-Crafts-type cyclization suggestt hat the mechanism of the planarizationr eactionp roceeds through extension of the p system. To appraise the doping effect of the boroxadizine unit on the optoelectronic properties of topology-equivalent molecular graphenes, the all-carbon and pyrylium PAHa nalogues, all featuring ag ulf-type periphery, were also prepared. As already shown for the borazinodoped hexabenzocoronene, the replacement of the central benzene ring by its B 3 N 2 Oc ongener widens the HOMO-LUMO gap and dramaticallye nhances the fluorescence quantum yield.[a] J. Scheme1.Synthetic planarizationp rotocols for preparing borazino-doped hexabenzocoronenes 1 and 2.Figure 7. ESP surfaces mapped on the vdW surface up to an electrondensity of 0.05 electronbohr À3 for a) 11 and b) 18.Side (up) and top (bottom) view of the packingo fc )11 and d) 18.Atom colors:pink B, blue N, red O, gray C. Spacegroups: P2 1 /c and P1.

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Doping Polycyclic Arenes with Nitrogen–Boron–Nitrogen (NBN) Units

Cited by 84 publications

References 32 publications

Concise Approach to T‐Shaped NBN‐Phenalene Cored Luminogens as Intensive Blue Light Emitters

Concise Approach to T‐Shaped NBN‐Phenalene Cored Luminogens as Intensive Blue Light Emitters

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Boron–Nitrogen‐Doped Nanographenes: A Synthetic Tale from Borazine Precursors

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