Cationic Boron Formazanate Dyes**

Maar, Ryan R.; Katzman, Benjamin D.; Boyle, Paul D.; Staroverov, Viktor N.; Gilroy, Joe B.

doi:10.1002/ange.202015036

“…BN aromatics have been widely investigated in recent years since the materials possess attractive physical and chemical properties and hold potential applications in the light-emitting polymer [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 ], semiconductor [ 13 , 14 , 15 , 16 , 17 ], and other research fields [ 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]; however, there have been relatively few reports on the synthesis of nitrated BN aromatics. Thus far, only five mononitro-BN aromatics have been reported [ 30 , 31 ].…”

Section: Introductionmentioning

confidence: 99%

Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization

Zhang

¹

,

Zuckerman

²

,

Pagoria

³

et al. 2021

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Mono- and dinitro-BN-naphthalenes, i.e., 1-nitro-, 3-nitro-, 1,6-dinitro-, 3,6-dinitro-, and 1,8-dinitro-BNN, were generated in the nitration of 9,10-BN-naphthalene (BNN), a boron–nitrogen (BN) bond-embedded naphthalene, with AcONO2 and NO2BF4 in acetonitrile. The nitrated products were isolated and characterized by NMR, GC-MS, IR, and X-ray single crystallography. The effects of the nitration on the electron density and aromaticity of BNN were evaluated by B-11 NMR analysis and HOMA calculations.

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Electrochromic Polycationic Organoboronium Macrocycles with Multiple Redox States

Shimoyama

¹

,

Baser‐Kirazli

²

,

Lalancette

³

et al. 2021

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Polycationic macrocycles are attractive as they display unique molecular switching capabilities arising from their redox properties. Although diverse polycationic macrocycles have been developed, those based on cationic boron systems remain very limited. We present herein the development of novel polycationic macrocycles by introducing organoboronium moieties into a conjugated organoboron macrocyclic framework. These macrocycles consist of four bipyridylboronium units that are connected by fluorene and either electron‐deficient arylborane or electron‐rich arylamine moieties. Electrochemical studies reveal that the macrocycles undergo reversible multi‐step redox processes with transfer of up to 10 electrons. Switchable electrochromic behavior is demonstrated via spectroelectrochemical studies and the observed color changes are rationalized by correlation with computed electronic transitions using DFT methods.

show abstract

Electrochromic Polycationic Organoboronium Macrocycles with Multiple Redox States

Shimoyama

¹

,

Baser‐Kirazli

²

,

Lalancette

³

et al. 2021

View full text Add to dashboard Cite

Polycationic macrocycles are attractive as they display unique molecular switching capabilities arising from their redox properties. Although diverse polycationic macrocycles have been developed, those based on cationic boron systems remain very limited. We present herein the development of novel polycationic macrocycles by introducing organoboronium moieties into a conjugated organoboron macrocyclic framework. These macrocycles consist of four bipyridylboronium units that are connected by fluorene and either electron-deficient arylborane or electron-rich arylamine moieties. Electrochemical studies reveal that the macrocycles undergo reversible multi-step redox processes with transfer of up to 10 electrons. Switchable electrochromic behavior is demonstrated via spectroelectrochemical studies and the observed color changes are rationalized by correlation with computed electronic transitions using DFT methods.Endowed with unique electrooptical characteristics, conjugated polycations serve as important components in the fields of supramolecular materials and redox-responsive systems. [1] Among them, polycationic macrocycles such as Stoddarts "blue box" [2] generate impressive interlocked structures and exhibit unique molecular switching capabilities. [3] Since their first discovery, numerous derivatives have been synthesized and utilized in supramolecular assemblies, host-guest chemistry, [4] molecular electronics, [5] electron transfer, [6] and electrochromic [7] materials. Although diverse polycationic macrocycles have been reported, [8] those based on cationic boronium moieties remain very limited. [9] Very recently, coordination-driven self-assembly to build up polycationic boron macrocycles was reported by Himmel and co-workers. [9c] These macrocycles are composed of cationic diborane units that are linked together by pyrazine, 4,4'-bipyridine, or 1,2di(4-pyridyl)ethene.Over the course of our studies on organoboron pconjugated materials, [10] we developed a unique class of boracyclophanes with strongly Lewis acidic boron sites, including ambipolar borazine A [11] with its alternating electron-deficient arylboranes and electron-rich arylamines and the highly electron-deficient macrocycles B [12] (Figure 1 a). [13]

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Cationic Boron Formazanate Dyes**

Cited by 3 publications

References 90 publications

Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization

Mono- and Dinitro-BN-Naphthalenes: Formation and Characterization

Electrochromic Polycationic Organoboronium Macrocycles with Multiple Redox States

Electrochromic Polycationic Organoboronium Macrocycles with Multiple Redox States

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