Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays

Zhou, W.; Sarma, Tridib; Yang, Liu; Lei, Chuanhu; Sessler, Jonathan L.

doi:10.1039/d2sc01635d

Cited by 7 publications

(3 citation statements)

References 52 publications

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“…Carbaporphyrin (X = CH) contains inner protons from the replaced carbon donor (sp 2 CH) and the nitrogen donor (sp 2 NH) of the pyrroles (Figure ). Two different kinds of inner protons in carbaporphyrins complementarily support the existing aromaticity; otherwise, the chemical shifts of NHs are sometimes affected by their strong hydrogen bonds, and their signals are not shown due to rapid exchange with other nitrogen atoms in NMR studies. We were also interested in determining the extent to which a specific E.W.…”

Section: Introductionmentioning

confidence: 99%

Effects of Electron-Withdrawing and Electron-Donating Groups on Aromaticity in Cyclic Conjugated Polyenes

Ko,

Roh,

Desale

et al. 2024

J. Am. Chem. Soc.

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Determining the aromaticity of various fluorinated benzenes is challenging as easily obtained experimental aromaticity [Δδ(H outer − H inner )] necessitates the chemical shifts of inner and outer protons. This issue was addressed in porphyrinoids by replacing the electron-withdrawing (E.W.) groups at the mesopositions of porphyrins and allyliporphyrins. Electronic effects on aromaticity in porphyrinoids have not been thoroughly examined in the literature. In porphyrins, the effect of E.W. groups is minimal, making it difficult to establish a clear relationship between the aromaticity strength and E.W. groups. Conversely, in allyliporphyrins, stronger E.W. groups, such as indandione (IND) derivatives, significantly reduce the aromaticity of the parent structure. The IND derivatives disrupted the aromatic pathway of allyliporphyrin more effectively than those attached to porphyrins. This is attributed to the absence of β-carbons in allyliporphyrins. The effect of electron-donating (E.D.) groups on porphyrins and allyliporphyrins was further investigated. Contrary to the initial assumption that the E.D. groups might enhance aromaticity owing to their ability to increase electron density, as the strength of the E.D. groups increased, the aromaticity of the porphyrinoids decreased. Despite the modest reduction in aromaticity, any form of electron perturbation reduces aromaticity. The aromaticity of various fluorinated benzenes is expected to parallel our observations of porphyrinoids as representative aromatic polyenes.

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Section: Introductionmentioning

confidence: 99%

Effects of Electron-Withdrawing and Electron-Donating Groups on Aromaticity in Cyclic Conjugated Polyenes

Ko,

Roh,

Desale

et al. 2024

J. Am. Chem. Soc.

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“…Over the past two decades, there has been growing interest in N-doped carbon-rich materials. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] These materials exhibit excellent characteristics and a wide range of applications, including ion recognition, optical materials, electronic devices, and catalysts. [18][19][20][21][22][23] A crucial strategy for generating these materials with precise structures is bottom-up organic synthesis.…”

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confidence: 99%

“…1 was characterized with high resolution mass spectrometry (HRMS) ([M + H] + calcd 457.0511; found: 457.0502), as well as 1 H and 13 C NMR spectroscopic study in CDCl 3 (Fig. S9, S10 and S14, ESI †).…”

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confidence: 99%

Pentatomic carbon ring conjugated nitrogen-doped nanographene

Bai,

Xu,

Wang

et al. 2024

Mater. Adv.

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Threading a Linear Molecule Through a Macrocycle Thanks to Boron: Optical Properties of the Threaded Species and Synthesis of a Rotaxane

Hicguet,

Verrieux,

Mongin

et al. 2024

Angewandte Chemie

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Two BODIPYs and two boron b‐diketonates were threaded through a macrocycle bearing a 2,2’‐biphenol unit, showing thus the ability of boron to act as a gathering atom. The new threaded species were characterized by 1D and 2D NMR spectroscopy as well as by X‐ray crystallography for one of them and their properties rationalized with quantum chemistry to unravel the vibronic contributions. The BODIPYs exhibited interesting fluorescence features with quantum yields up to 91% and enhanced photostability compared to their non‐threaded homologues. A rotaxane was synthesized using this threading strategy after stoppering and removing the boron with potassium hydroxide.

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Controlled assembly of a bicyclic porphyrinoid and its 3-dimensional boron difluoride arrays

Abstract: A fully conjugated cryptand-like bicyclic porphyrinoid ligand 4, incorporating three carbazole linkages and four dipyrrin moieties, was prepared via the acid-catalysed condensation of an extended 2,2’-bipyrrole analogue containing a central...

Cited by 7 publications

References 52 publications

Effects of Electron-Withdrawing and Electron-Donating Groups on Aromaticity in Cyclic Conjugated Polyenes

Effects of Electron-Withdrawing and Electron-Donating Groups on Aromaticity in Cyclic Conjugated Polyenes

Pentatomic carbon ring conjugated nitrogen-doped nanographene

Threading a Linear Molecule Through a Macrocycle Thanks to Boron: Optical Properties of the Threaded Species and Synthesis of a Rotaxane

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