New Heteroaromatic Compounds. XXI.<sup>1</sup> Some Tetracyclic Systems<sup>2</sup>

Dewar, Michael J. S.; Poesche, W. H.

doi:10.1021/jo01030a023

Cited by 46 publications

(19 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2). 12,13 The significant BQN multiple bond character in these intermediates considerably reduces the Lewis acidity at boron and thus an additional Lewis acid (e.g. AlCl 3 ) was required as a catalyst to generate a more reactive boron electrophile able to effect C-H borylation.…”

Section: Intramolecular Electrophilic C-h Borylation: the Early Yearsmentioning

confidence: 99%

“…Other notable observations from these early studies include the formation of a single BN containing borylated product when commencing from aniline derivatives containing multiple proximal sites that could feasibly undergo directed electrophilic C-H borylation (Scheme 1, H a and H b can both be substituted). 13 For example, compound 6 is formed exclusively with no compound C observed. This indicates that steric effects are important in controlling the overall outcome from R 2 N-directed intramolecular C-H borylation under these conditions, with no products from C-H borylation of the more hindered peri position (H a ) observed despite this position generally being more reactive in S E Ar reactions.…”

Section: Intramolecular Electrophilic C-h Borylation: the Early Yearsmentioning

confidence: 99%

See 1 more Smart Citation

Intramolecular (directed) electrophilic C–H borylation

et al. 2020

View full text Add to dashboard Cite

show abstract

Section: Intramolecular Electrophilic C-h Borylation: the Early Yearsmentioning

confidence: 99%

Section: Intramolecular Electrophilic C-h Borylation: the Early Yearsmentioning

confidence: 99%

Intramolecular (directed) electrophilic C–H borylation

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Presumably in the intermediate adduct formed by 2‐2′diaminobiphenyl and phenylboron dichloride, the positively charged nitrogen atoms deactivated the adjacent benzene rings, so that no electrophilic cyclization took place. Similarly, the 4,5‐azaborapyrene 7 a was also successfully synthesized from 4‐aminophenanthrene and BCl 3 15. Compound 7 a was then converted to other BN‐pyrene derivatives ( 7 b – e ).…”

Section: Early Work On Bn‐substituted Pahs (1950s–1960s)mentioning

confidence: 99%

BN Heterosuperbenzenes: Synthesis and Properties

Wang

Pei

2014

Chemistry A European J

404

149

View full text Add to dashboard Cite

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.

show abstract

“…Further modification on the B atom led to a series of BN-substituted phenanthrene derivatives ( 39 ). Consequently, a family of B-N embedded PAHs was synthesized via the similar strategies (Dewar and Dietz, 1959 ; Chissick et al, 1960 ; Dewar and Poesche, 1963 , 1964 ). In 2013, Pei and coworkers reported BN-substituted tetrathienonaphthalene derivatives ( 41 ) (Wang X. Y. et al, 2013 ), starting from 40 by adding BBr 3 and Et 3 N. BBr 3 attacked the imine and consequently electrophilic attacked the β-site of thiophene to finish the cyclization.…”

Section: Synthesis Routesmentioning

confidence: 99%

BN Embedded Polycyclic π-Conjugated Systems: Synthesis, Optoelectronic Properties, and Photovoltaic Applications

Huang

2018

Front. Chem.

114

View full text Add to dashboard Cite

In the periodic table of elements, boron (B, atomic number, 5) and nitrogen (N, atomic number, 7) are neighboring to the carbon (C, atomic number, 6). Thus, the total electronic number of two carbons (12) is equal to the electronic sum of one boron (5) and one nitrogen (7). Accordingly, replacing two carbons with one boron and one nitrogen in a π-conjugated structure gives an isoelectronic system, i.e., the BN perturbed π-conjugated system, comparing to their all-carbon analogs. The BN embedded π-conjugated systems have unique properties, e.g., optical absorption, emission, energy levels, bandgaps, and packing order in contrast to their all-carbon analogs and have been intensively studied in terms of novel synthesis, photophysical characterizations, and electronic applications in recent years. In this review, we try to summarize the synthesis methods, optoelectronic properties, and progress in organic photovoltaic (OPV) applications of the representative BN embedded polycyclic π-conjugated systems. Firstly, the narrative will be commenced with a general introduction to the BN units, i.e., B←N coordination bond, B-N covalent bond, and N-B←N group. Then, the representative synthesis strategies toward π-conjugated systems containing B←N coordination bond, B-N covalent bond, and N-B←N group will be summarized. Afterwards, the frontier orbital energy levels, optical absorption, packing order in solid state, charge transportation ability, and photovoltaic performances of typical BN embedded π-conjugated systems will be discussed. Finally, a prospect will be proposed on the OPV materials of BN doped π-conjugated systems, especially their potential applications to the small molecules organic solar cells.

show abstract

New Heteroaromatic Compounds. XXI.¹ Some Tetracyclic Systems²

Cited by 46 publications

References 3 publications

Intramolecular (directed) electrophilic C–H borylation

Intramolecular (directed) electrophilic C–H borylation

BN Heterosuperbenzenes: Synthesis and Properties

BN Embedded Polycyclic π-Conjugated Systems: Synthesis, Optoelectronic Properties, and Photovoltaic Applications

Contact Info

Product

Resources

About

New Heteroaromatic Compounds. XXI.1 Some Tetracyclic Systems2

Cited by 46 publications

References 3 publications

Intramolecular (directed) electrophilic C–H borylation

Intramolecular (directed) electrophilic C–H borylation

BN Heterosuperbenzenes: Synthesis and Properties

BN Embedded Polycyclic π-Conjugated Systems: Synthesis, Optoelectronic Properties, and Photovoltaic Applications

Contact Info

Product

Resources

About

New Heteroaromatic Compounds. XXI.¹ Some Tetracyclic Systems²