Accessing Two-Stage Regioselective Photoisomerization in Unsymmetrical N,C-Chelate Organoboron Compounds: Reactivity of B(ppz)(Mes)Ar

Li, Cally; Mellerup, Soren K.; Wang, Xiang

doi:10.1021/acs.organomet.8b00598

Cited by 11 publications

(4 citation statements)

References 41 publications

(43 reference statements)

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“…7). [77][78][79][80][81][82][83][84][85] Li and co-workers further explored the photoisomerization reaction using theoretical studies. 86,87 In 2019, the Wang group 88 reported the synthesis of five pairs of regioisomers (53)(54)(55)(56)(57) based on the indolizino [3,4,5-ab] isoindole backbone as shown in Fig.…”

Section: Nc-chelate B-n Coordinated Boron Compoundsmentioning

confidence: 99%

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Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

2022

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Section: Nc-chelate B-n Coordinated Boron Compoundsmentioning

confidence: 99%

“…7). 77–85 Li and co-workers further explored the photoisomerization reaction using theoretical studies. 86,87…”

Section: Nc-chelate B–n Coordinated Boron Compoundsmentioning

confidence: 99%

Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

2022

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“…Several other studies have been carried out to obtain an in-depth knowledge of such chromophores and more can be found in references [38,[41][42][43][44][45][46]. Through various structural modifications and analogues, it has been established that photoisomerization could also be extended to N^C-chelate in addition to the ppy systems [47]. For instance, in a recent work, Wang and coworkers [47] replaced pyridine by a pyrazole as the N-donor (8, Figure 6) and reported its two-stage photoreactivity.…”

Section: -Arylpyridine-derived N^c-chelatesmentioning

confidence: 99%

“…Through various structural modifications and analogues, it has been established that photoisomerization could also be extended to NˆC-chelate in addition to the ppy systems [47]. For instance, in a recent work, Wang and coworkers [47] replaced pyridine by a pyrazole as the N-donor (8, Figure 6) and reported its two-stage photoreactivity. These new systems undergo photoisomerization to produce thermally stable aza borata bisnorcaradienes (8a), which upon prolonged irradiation led to isomerize products 14aH-diazabor-epins or BNN-benzotropilidene (8b).…”

Section: -Arylpyridine-derived N^c-chelatesmentioning

confidence: 99%

Recent Advances in π-Conjugated N^C-Chelate Organoboron Materials

et al. 2020

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Boron-containing π-conjugated materials are archetypical candidates for a variety of molecular scale applications. The incorporation of boron into the π-conjugated frameworks significantly modifies the nature of the parent π-conjugated systems. Several novel boron-bridged π-conjugated materials with intriguing structural, photo-physical and electrochemical properties have been reported over the last few years. In this paper, we review the properties and multi-dimensional applications of the boron-bridged fused-ring π-conjugated systems. We critically highlight the properties of π-conjugated N^C-chelate organoboron materials. This is followed by a discussion on the potential applications of the new materials in opto-electronics (O-E) and other areas. Finally, attempts will be made to predict the future direction/outlook for this class of materials.

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Photochemical Transformations Involving Organoboron

Mellerup

Wang

2019

Patai's Chemistry of Functional Groups

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Boron gets its name from the term borax, the mineral from which it was originally isolated, by analogy with carbon due to their chemical similarities. Unlike its neighbor on the periodic table, however, boron only possesses enough valence electrons to form three covalent bonds. This means that organoboron compounds are inherently electron deficient and typically adopt a trigonal‐planar (sp 2 ‐hybridized) geometry with the empty p z orbital of boron lying orthogonal to the bonding plane. In this form, boron is isoelectronic and isostructural with a positively charged carbocation, which gives rise to many of the applications often associated with trivalent organoboranes (e.g., organic synthons and electron‐transport materials). Coordinatively saturating these systems with anionic or neutral Lewis bases yields tetrahedral, four‐coordinated boron compounds with a formal negative charge. This new bonding arrangement significantly alters the orbital composition of the resulting molecules, imparting new features such as intense charge transfer (CT) luminescence and, in some cases, unique photochemical reactivities such as photochromism or photoelimination. This chapter will document recent progress in photochemical transformation based on organoboron compounds. A brief overview of concepts related to photophysical and photochemical processes will be presented, followed by an introduction to photochromic systems and a comprehensive review of organoboron photochemistry. Several recently discovered classes of photoresponsive organoboron molecules and their potential applications will be presented.

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Accessing Two-Stage Regioselective Photoisomerization in Unsymmetrical N,C-Chelate Organoboron Compounds: Reactivity of B(ppz)(Mes)Ar

Cited by 11 publications

References 41 publications

Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

Recent advances in the synthesis of luminescent tetra-coordinated boron compounds

Recent Advances in π-Conjugated N^C-Chelate Organoboron Materials

Photochemical Transformations Involving Organoboron

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