Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

White, Brittany M.; Yu, Zhiwen; Kawashima, Taryn E.; Branchaud, Bruce B.; Pluth, Michael D.; Jasti, Ramesh

doi:10.26434/chemrxiv.6261884

Cited by 10 publications

(19 citation statements)

References 43 publications

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“…These studies have mainly focused on the influence of the nanoring size and of the building units on the structural, electronic and chiral properties. [3][4][5][6][7][8][9][10][11][12][13][14] As recently reviewed by Jasti and coworkers, 15 nanorings can cover a broad range of applications including imaging tools in biology, 16 complexing agent for single-walled carbon nanotubes 17 or fullerenes, [18][19][20] carbon-based porous material, [21][22] solid state emitters, 11,[23][24] or spin crossover compounds. 25 Molecular nanorings are now considered for their potential applications in organic electronics.…”

Section: Introductionmentioning

confidence: 99%

[4]Cyclo-N-alkyl-2,7-carbazoles: Influence of the Alkyl Chain Length on the Structural, Electronic, and Charge Transport Properties

et al. 2021

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Macrocycles possessing radially oriented π−orbitals have experienced a fantastic development. However, their incorporation in organic electronic devices remains very scarce. In this work, we aim at bridging the gap between organic electronics and nanorings by reporting the first detailed structure-properties-device performance relationship study of organic functional materials based on a nanoring system. Three [4]cyclo-N-alkyl-2,7-carbazoles bearing different alkyl chains on their nitrogen atoms have been synthesized and characterized by combined experimental and theoretical approaches. This study includes electrochemical, photophysical, thermal and structural solid-state measurements and charge transport properties investigations. An optimized protocol of the Pt approach has been developed to synthesize the [4]-cyclocarbazoles in high yield (52-64%), of great interest for further development of nanorings especially in materials science. The charge transport properties of [4]-cyclocarbazoles and a model compound, [8]-cycloparaphenylene ([8]CPP), have been studied. Although no field effect (FE) mobility was recorded for benchmark [8]CPP, FE mobility values of ca 10 -5 cm².V -1 .s -1 were recorded for the [4]-cyclocarbazoles. The characteristics (threshold voltage VTH, subthreshold swing SS, trapping energy ∆E) recorded for the three[4]-cyclocarbazoles appear to be modulated by the alkyl chain length borne by the nitrogen atoms. Remarkably, the space-charge-limited current mobilities measured for the [4]-cyclocarbazoles are about 3 orders of magnitude higher than that of [8]CPP (1.37/ 2.78×10 -4 for the [4]-cyclocarbazoles vs 1.21×10 -7 cm².V -1 .s -1 for [8]CPP) highlighting the strong effect of nitrogen bridges on the charge transport properties. The whole study opens the way to the use of nanorings in electronics, which is now the next step of their developments.

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Section: Introductionmentioning

confidence: 99%

[4]Cyclo-N-alkyl-2,7-carbazoles: Influence of the Alkyl Chain Length on the Structural, Electronic, and Charge Transport Properties

et al. 2021

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“…For example, substructures of CNTs, often referred to as carbon nanohoops (2) and carbon nanobelts (3)(4)(5), can now be prepared in which the size (6), connectivity (7), and even heteroatom doping (8) can be controlled with atomic precision. These molecular nanocarbons are gaining traction for a wide array of possible applications in organic electronics, biology and polymer science (9)(10)(11)(12)(13). A particularly exciting avenue is to use organic synthetic methods to prepare topologically unique carbon nanomaterials -in particular, mechanically interlocked structures.…”

Section: Main Textmentioning

confidence: 99%

Active Template Strategy for the Preparation of Interlocked Nanocarbons

May¹,

Raden²,

Maust³

et al. 2022

Preprint

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Mechanically interlocked carbon nanostructures represent a relatively unexplored frontier in carbon nanoscience due to the difficulty in preparing these unusual topological materials. Here we illustrate an active template method in which the key mechanical bond forming step is accomplished by leveraging unique ligand motifs to catalyze a cross-coupling reaction within the pore of a macrocycle. Once the mechanical bond has been formed, these macrocyclic ligands can then be converted into pi-conjugated structures in a subsequent synthetic step. This method provides a general strategy by which a variety of mechanically interlocked carbon nanostructures can be prepared which will enable structure-property relationships to be established for this emerging class of nanomaterials.

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“…[8][9][10][11] While CPPs were imaginary molecules until 2009, CPPs with various sizes (n = 5-16, 18, 20, 21) are now being synthesized with the development of the innovative synthetic methods by Bertozzi/Jasti, 12 Itami, 13 Yamago, 14,15 and Osakada/Tsuchido 16 (Figure 1). Furthermore, these works unveiled unique size-dependent physical properties 17 and applications of CPPs, i.e., circularly polarized luminescent (CPL) materials, [18][19][20][21] biological fluorophores, 22,23 gas-adsorption materials, [24][25][26] and electron-transport materials. 27 In addition, CPPs have also been used to construct unique molecular architectures, [28][29][30] such as supramolecular host-guest molecules, [31][32][33][34][35][36][37] mechanically interlocked molecules (MIMs), [38][39][40] and building blocks for tubular nanostructures.…”

Section: Introductionmentioning

confidence: 99%

Dynamic Au–C σ-Bonds Leading to an Efficient Synthesis of [n]Cycloparaphenylenes (n = 9 – 15) by a Self-Assembly

Tanji

Yoshigoe

Saito

et al. 2022

Preprint

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The transmetalation of the digold(I) complex [Au2Cl2(dcpm)] (1) (dcpm = bis(dicyclohexylphosphino)methane) with oligophenylene diboronic acids gave the triangular macrocyclic complexes [Au2(C6H4)x(dcpm)]3 (x = 3, 4, 5) with yields of over 70%. On the other hand, when the other digold(I) complex [Au2Cl2(dppm)] (1') (dcpm = bis(diphenylphosphino)methane) was used, only a negligible amount the triangular complex was obtained. The control experiments revealed that the dcpm ligand accelerated an intermolecular Au(I)–C σ-bond-exchange reaction, and that this high reversibility is the origin of the selective formation of the triangular complexes. Structural analyses and theoretical calculations indicate that dcpm ligand increases the electrophilicity of the Au atom in the complex, thus facilitating the exchange reaction, though cyclohexyl group is an electron-donating group. Furthermore, the oxidative chlorination of the macrocyclic gold complexes afforded a series of [n]cycloparaphenylenes (n = 9, 12, 15) in 78–88% isolated yields. The reaction of two different macrocyclic Au complexes gave a mixture of macrocyclic complexes incorporating different oligophenylene linkers, from which a mixture of [n]cycloparaphenylenes with various numbers of phenylene units was obtained in good yields.

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Expanding the Chemical Space of Biocompatible Fluorophores: Nanohoops in Cells

Cited by 10 publications

References 43 publications

[4]Cyclo-N-alkyl-2,7-carbazoles: Influence of the Alkyl Chain Length on the Structural, Electronic, and Charge Transport Properties

[4]Cyclo-N-alkyl-2,7-carbazoles: Influence of the Alkyl Chain Length on the Structural, Electronic, and Charge Transport Properties

Active Template Strategy for the Preparation of Interlocked Nanocarbons

Dynamic Au–C σ-Bonds Leading to an Efficient Synthesis of [n]Cycloparaphenylenes (n = 9 – 15) by a Self-Assembly

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