Effect of curvature and placement of donor and acceptor units in cycloparaphenylenes: a computational study

Lovell, Terri C.; Fosnacht, Kaylin G; Colwell, Curtis; Jasti, Ramesh

doi:10.1039/d0sc03923c

Cited by 24 publications

(33 citation statements)

References 37 publications

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“…In 2014, Tandon and co-workers [79] reported an efficient and concise one-pot regio-and chemo-selective synthesis of benzo[a]phenazine and derivatives (11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24). As shown in Scheme 3, this method was employed for 2, 3-dichloro-1, 4-naphoquinone to nucleophile with ophenylenediamine and benzamidine under the condition of H 2 O in the presence of alkali and micelles (SDS) as catalysts, achieving the expected products in excellent yields.…”

Section: Benzo[a]phenazine and Derivativesmentioning

confidence: 99%

“…Since then, a plenteous of phenazine derivatives have been synthesized and identified due to their attractive performance [15][16][17][18][19]. According to the documents [20][21][22][23][24][25][26], it was firstly reported in the nineteenth century. Then, the systematically synthetic methodologies about the phenazine derivatives have been advanced in recent years [27][28][29][30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

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Synthetic strategies of phenazine derivatives: A review

Che

et al. 2022

Journal of Heterocyclic Chem

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Since the growing importance of phenazine derivatives, the efficient synthetic strategies for the preparation of phenazine derivatives have attracted great attention from organic methodology. Herein, we comprehensively review and summarize a series of sustainable and facile synthetic strategies of phenazine derivatives. Moreover, we further discuss the approach of preparation and the superiority of each strategy.

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Section: Benzo[a]phenazine and Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic strategies of phenazine derivatives: A review

Che

et al. 2022

Journal of Heterocyclic Chem

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“…Tuning of these properties is necessary for potential applications of CPPs (e.g., as fluorescent probes). 29,[46][47][48][49] The second approach involves steric confinement of the macrocycle center, which can also influence binding. Top and bottom rim functionalization can transform the open space inside a CPP-type macrocycle into a confined space, leading to multiple contacts between host and guest.…”

Section: Synpacts Synlettmentioning

confidence: 99%

Confining the Inner Space of Strained Carbon Nanorings

Grabicki¹,

Dumele²

2021

Synlett

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Strained aromatic macrocycles based on cycloparaphenylenes (CPPs) are the shortest repeating units of armchair single-walled carbon nanotubes. Since the development of several new synthetic methodologies for accessing these structures, their properties have been extensively studied. Besides the fundamental interest in these novel molecular scaffolds, their application in the field of materials science is an ongoing topic of research. Most of the reported CPP-type macrocycles display strong binding toward fullerenes, due to the perfect match between the convex and concave π-surfaces of fullerenes and CPPs, respectively. Highly functionalized CPP derivatives capable of supramolecular binding with other molecules are rarely reported. The synthesis of highly functionalized [n]cyclo-2,7-pyrenylenes leads to CPP-type macrocycles with a defined cavity capable of binding non-fullerene guests with high association constants.

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“…This is in stark contrast to xanthene, cyanine, and BODIPY dyes . Additionally, the controlled nanohoop synthesis permits facile tuning of fluorescence properties. − Recently, it was shown by theory that these materials can be engineered to have near-infrared emissions, further expanding their capabilities . These characteristics position nanohoops as promising fluorescent scaffolds for biological applications.…”

Section: Introductionmentioning

confidence: 99%

“…29−33 Recently, it was shown by theory that these materials can be engineered to have nearinfrared emissions, further expanding their capabilities. 31 These characteristics position nanohoops as promising fluorescent scaffolds for biological applications.…”

Section: Introductionmentioning

confidence: 99%

Subcellular Targeted Nanohoop for One- and Two-Photon Live Cell Imaging

et al. 2021

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Fluorophores are powerful tools for interrogating biological systems. Carbon nanotubes (CNTs) have long been attractive materials for biological imaging due to their nearinfrared excitation and bright, tunable optical properties. The difficulty in synthesizing and functionalizing these materials with precision, however, has hampered progress in this area. Carbon nanohoops, which are macrocyclic CNT substructures, are carbon nanostructures that possess ideal photophysical characteristics of nanomaterials, while maintaining the precise synthesis of small molecules. However, much work remains to advance the nanohoop class of fluorophores as biological imaging agents. Herein, we report an intracellular targeted nanohoop. This fluorescent nanostructure is noncytotoxic at concentrations up to 50 μM, and cellular uptake investigations indicate internalization through endocytic pathways. Additionally, we employ this nanohoop for two-photon fluorescence imaging, demonstrating a high two-photon absorption cross-section (65 GM) and photostability comparable to a commercial probe. This work further motivates continued investigations into carbon nanohoop photophysics and their biological imaging applications.

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Effect of curvature and placement of donor and acceptor units in cycloparaphenylenes: a computational study

Abstract: Cycloparaphenylenes have promise as novel fluorescent materials. However, shifting their fluorescence beyond 510 nm is difficult. Herein, we computationally explore the effect of incorporating electron accepting and electron donating units...

Cited by 24 publications

References 37 publications

Synthetic strategies of phenazine derivatives: A review

Synthetic strategies of phenazine derivatives: A review

Confining the Inner Space of Strained Carbon Nanorings

Subcellular Targeted Nanohoop for One- and Two-Photon Live Cell Imaging

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