Determination of Enantiomeric Purity of Single-Wall Carbon Nanotubes Using Flavin Mononucleotide

Wei, Xiaojun; Tanaka, Takeshi; Hirakawa, Toshiki; Yomogida, Yohei; Kataura, Hiromichi

doi:10.1021/jacs.7b09142

Cited by 35 publications

(68 citation statements)

References 32 publications

(22 reference statements)

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“… The selective synthesis of either SWNT enantiomer has not been successful as yet It is difficult to evaluate the enantiomeric purity where any enantiomeric components contained in an enantiomeric mixture cannot be recognized; therefore, the high purity SWNT enantiomer will open the gate towards clear chiral separation and chiral molecule synthesis This is study will help us to solve the structural polydispersity problem of SWNT …”

Section: Introductionmentioning

confidence: 99%

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Assignment of the Absolute‐Handedness Chirality of Single‐Walled Carbon Nanotubes by Using Organic Molecule Supramolecular Structures

El‐Mageed

Handayani

Chen

et al. 2018

Chemistry A European J

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Supramolecular structures of organic molecules on planar nanocarbon surfaces, such as highly oriented pyrolytic graphite (HOPG), have been extensively studied and the factors that control them are generally well‐established. In contrast, the properties of supramolecular structures on curved nanocarbon surfaces like carbon nanotubes remain challenging to predict and/or to understand. This paper reports an investigation into the first study of the supramolecular structures of 5,15‐bisdodecylporphyrin (C12P) on chiral, concentrated single‐walled carbon nanotubes (SWNTs; with right‐handed helix P‐ and left‐handed helix M‐) surfaces using STM. Furthermore, the study is the first of its kind to experimentally assign the absolute‐handedness chirality of SWNTs, as well as to understand their effect on the supramolecular structures of organic molecules on their surfaces. Interestingly, these SWNT enantiomers resulted in supramolecular structures of opposite chirality based on the handedness chirality. With molecular modelling, we predicted the absolute‐handedness chirality of SWNTs, before demonstrating this experimentally.

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Section: Introductionmentioning

confidence: 99%

“…It is difficult to evaluate the enantiomeric purity where any enantiomeric components contained in an enantiomeric mixture cannot be recognized; therefore, the high purity SWNT enantiomer will open the gate towards clear chiral separation and chiral molecule synthesis …”

Section: Introductionmentioning

confidence: 99%

Assignment of the Absolute‐Handedness Chirality of Single‐Walled Carbon Nanotubes by Using Organic Molecule Supramolecular Structures

El‐Mageed

Handayani

Chen

et al. 2018

Chemistry A European J

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show abstract

Section: Toward Enantiomerically Pure Swcntsmentioning

confidence: 99%

“…Using optical absorbance and CD spectra, FMN was observed to induce a handedness-dependent shift in the E 11 optical transition that is linearly correlated with enantiomeric purity. [197] Figure 6d shows an example CD spectra and how its intensity changes for different (6,5) SWCNT enantiomer concentrations when coupled to FMN. This strategy enables direct measurement of enantiomeric purity for any mixture of (6,5) SWCNT enantiomers using only CD characterization, suggesting a generalized method for high-throughput SWCNT enantiomeric purity characterization.…”

Section: Wwwadvmatde Wwwadvancedsciencenewscommentioning

confidence: 99%

Chirality‐Enriched Carbon Nanotubes for Next‐Generation Computing

Rojas

Hersam

2020

Advanced Materials

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electronic, [3-4,4] and functional requirements. [5] Conventional silicon integrated circuit (IC) technology faces significant challenges in meeting these demands due to its limited mechanical flexibility, high temperature processing, and scaling limitations. Emerging alternative computing platforms based on other crystalline semiconductors suffer from similar limitations. Consequently, nextgeneration computing necessitates the exploration of radically different electronic materials. Single-walled carbon nanotubes (SWCNTs) are among the most promising and highly studied nanoelectronic materials. Due to their small size, [6,7] solutionprocessability, [8] chemical stability, [9] and chirality-dependent optoelectronic properties, [10] SWCNTs offer a number of unique advantages and are compatible with the complex requirements of future computing devices. Recent advances in chiral enrichment of polydisperse SWCNTs [8,10] have allowed their use as semiconducting channels in diverse settings including charge transport devices, [2] optical emitters and detectors, [11,12] and chemical sensors. [2,3,13,14] With this tunable functionality, a range of SWCNT-based computing applications have been realized, such as printed digital logic, [15] sub-10 nm complementary metal-oxide-semiconductor (CMOS) field-effect transistors (FETs), [16] neuromorphic devices, [17] single-photon emitters (SPE), [18] and enantiomer-recognition sensors. [14] Herein, we discuss recent advances in SWCNT-based computing technologies that process, manage, and communicate information, with an emphasis on the enabling role of chiral enrichment. Section 2.1 defines the different levels of chiral enrichment. Sections 2.2 and 2.3 describe direct growth methods and post-processing purification of SWCNTs for electronic-type and monochiral enrichment. Section 3 discusses applications of electronic-type-enriched SWCNTs such as wearables, highly scaled FETs, 3D logic-memory integration, and neuromorphic devices. Section 4 outlines applications of monochiral-enriched SWCNTs including monochiral FETs, optical emitters, photodetectors, and optoelectronic ICs. Section 5 considers recent progress toward enantiomerically pure SWCNTs. Finally, Section 6 presents an outlook for SWCNTs in next-generation computing applications including a delineation of remaining challenges and future opportunities. For the past half century, silicon has served as the primary material platform for integrated circuit technology. However, the recent proliferation of nontraditional electronics, such as wearables, embedded systems, and lowpower portable devices, has led to increasingly complex mechanical and electrical performance requirements. Among emerging electronic materials, single-walled carbon nanotubes (SWCNTs) are promising candidates for next-generation computing as a result of their superlative electrical, optical, and mechanical properties. Moreover, their chirality-dependent properties enable a wide range of emerging electronic applications including sub-10 nm complementary fie...

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“…The enantiomer purity, based on the CD-spectra (Figure 5a) was calculated for both enantiomer fractions to be ~80 % (see Supplementary Figure S9). 63,64 Further surface exchange to (GT)40 ssDNA yielded defined enantiomer-pure ssDNA-SWCNT conjugates, used for sensing experiments (Figure 5a and 5b). No significant differences between the stereoisomers were found, while (GT)40-(-)-(6,5)-SWCNTs reacted with a stronger response to ascorbic acid, than (GT)40-(+)-(6,5)-SWCNTs ( Figure 5d) for ascorbic acid.…”

Section: Sensitivity Of Monochiral Sensors Chemical Sensing Withmentioning

confidence: 99%

Sensing with Chirality Pure near Infrared Fluorescent Carbon Nanotubes

Nißler¹,

Kurth²,

Li³

et al. 2020

Preprint

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Semiconducting single wall carbon nanotubes (SWCNTs) fluoresce in the near infrared (NIR) and the emission wavelength depends on their chirality (n,m). Interactions with the environment affect the fluorescence and can be tailored by functionalizing SWCNTs with biopolymers such as DNA, which is the basis for fluorescent biosensors. So far, such biosensors were mainly assembled from mixtures of SWCNT chiralities with large spectral overlap, which affects sensitivity as well as selectivity and prevents multiplexed sensing. The main challenge to gain chirality pure sensors has been to combine approaches to isolate specific SWCNTs and generic (bio)functionalization approaches. Here, we created chirality pure SWCNT-based NIR biosensors for important analytes such as neurotransmitters and investigated the impact of SWCNT chirality/handedness as well as long-term stability and sensitivity. For this purpose, we used aqueous two-phase extraction (ATPE) to gain chirality pure (6,5)-, (7,5)-, (9,4)- and (7,6)- SWCNTs (emission at ~ 990, 1040, 1115 and 1130 nm). Exchange of the surfactant sodium deoxycholate (DOC) to specific singlestranded (ss)DNA sequences yielded monochiral sensors for small analytes (dopamine, riboflavin, ascorbic acid, pH). DOC used in the separation process was completely removed because residues impaired sensing. The assembled monochiral sensors were up to 10 times brighter than their non-purified counterparts and the ssDNA sequence affected absolute fluorescence intensity as well as colloidal (long-term) stability and selectivity for the analytes. (GT)40-(6,5)-SWCNTs displayed the maximum fluorescence response to the neurotransmitter dopamine (+140 %, Kd = 1.9 x10-7 M) and a long-term stability > 14 days. Furthermore, the specific ssDNA sequences imparted selectivity to the analytes independent of SWCNT chirality and handedness of (+/-) (6,5)-SWCNTs. These monochiral/single-color SWCNTs enabled ratiometric/multiplexed sensing of dopamine, riboflavin, H2O2 and pH. In summary, we demonstrated the assembly, characteristics and potential of monochiral (single-color) SWCNTs for multiple NIR fluorescent sensing applications.

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Determination of Enantiomeric Purity of Single-Wall Carbon Nanotubes Using Flavin Mononucleotide

Cited by 35 publications

References 32 publications

Assignment of the Absolute‐Handedness Chirality of Single‐Walled Carbon Nanotubes by Using Organic Molecule Supramolecular Structures

Assignment of the Absolute‐Handedness Chirality of Single‐Walled Carbon Nanotubes by Using Organic Molecule Supramolecular Structures

Chirality‐Enriched Carbon Nanotubes for Next‐Generation Computing

Sensing with Chirality Pure near Infrared Fluorescent Carbon Nanotubes

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