Supramolecular interactions of fluorene-based copolymers containing 3,4-propylenedioxythiophene and phenazine units with SWNTs

Imit, Mokhtar; Imin, Patigul; Adronov, Alex

doi:10.1039/c6py00730a

Cited by 11 publications

(14 citation statements)

References 78 publications

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“…As one may point out, such a result demonstrates that many dispersion mechanisms can be possible with this particular helical ladder polymerthe most obvious being that SWCNTs can be entangled in helical pitches of the polymers. This mechanism should sort specifically s-SWCNTs as it does for other electron-rich systems. − On the other hand, both s- and c-SWCNTs can penetrate inside the helical polymer, which would lead to the dispersion of both conducting and semiconducting SWCNTs and explain the present results, as shown in Figure S25b. Further investigations will focus on the synthesis of an electron-rich helical ladder polymer with smaller cavities.…”

Section: Resultsmentioning

confidence: 63%

Helical Conjugated Ladder Polymers: Tuning the Conformation and Properties through Edge Design

Daigle

Morin

2017

Macromolecules

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Two helical conjugated ladder polymers (CLPs) have been synthesized using the photochemical cyclo-dehydrochlorination (CDHC) reaction on polychlorinated polymer derivatives. UV–vis and photoluminescence spectroscopy revealed that the outer chlorinated rings (phenyl or thiophene) used for the ladderization step have a significant impact on the conformation and electronic properties of the resulting polymers. The thiophene-embedded CLP exhibits strong intermolecular interactions and excimer-like emission due to a loose coil conformation while the all-phenyl CLP exhibits a tightly packed coil conformation. The helical CLPs also show good affinity toward HiPco carbon nanotubes (CNTs) as stable dispersions were prepared.

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Section: Resultsmentioning

confidence: 63%

Helical Conjugated Ladder Polymers: Tuning the Conformation and Properties through Edge Design

Daigle

Morin

2017

Macromolecules

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“…[7][8][9] On the other hand, the generation of noncovalent SWNT hybrids has promoted the fabrication of SWNT/field-effect transistor (FET) devices with appealing conductivity and tunable photosensitizationp roperties. [13][14][15][16][17][18][19][20][21][22] Despite all these success stories, the overwhelmingm ajority of reports on noncovalent derivatives of SWNTsa re based exclusivelyo nq ualitative experimental observations. [13][14][15][16][17][18][19][20][21][22] Despite all these success stories, the overwhelmingm ajority of reports on noncovalent derivatives of SWNTsa re based exclusivelyo nq ualitative experimental observations.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, the generation of noncovalent SWNT hybrids has promoted the fabrication of SWNT/field‐effect transistor (FET) devices with appealing conductivity and tunable photosensitization properties . Oligo‐ or polymeric structures have also been used, and have been particularly successful at addressing the sorting of SWNTs according to their diameter/chirality …”

Section: Introductionmentioning

confidence: 99%

Understanding Noncovalent Interactions of Small Molecules with Carbon Nanotubes

Calbo

López‐Moreno

Juan

et al. 2017

Chemistry A European J

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We combine experimental methods, density functional theory (DFT) calculations, and molecular dynamics (MD) simulations in the quantitative analysis of noncovalent interactions between (6,5)-enriched single-walled carbon nanotubes (SWNTs), as hosts, and a set of pyrene derivatives with different electronic properties and surface areas, as guests. The experiments and calculations were carried out in two solvents with markedly different polarities, namely 1,1',2,2'-tetrachloroethane (TCE) and N,N-dimethylformamide (DMF). Our results show that dispersion forces govern the supramolecular association of small molecules with (6,5)-SWNTs, with negligible contributions from ground-state charge-transfer effects. In the nonpolar solvent (TCE), the binding constants are highly correlated with the contact area between the SWNT and the guests. In the polar solvent (DMF), the binding constants show a complex dependence on the chemical nature of the pyrene substituents, as demonstrated by MD simulations with the explicit inclusion of solvent molecules. The solvation of the small molecules is shown to play a leading role in the binding process. Remarkably, the binding constants obtained from the MD simulations for the five guest molecules correlate with those derived from experiment. Furthermore, the MD simulations also reveal the structure of the adsorbed guest from low to high SWNT surface coverage.

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“…The donor–spacer–primary acceptor (D) – (S)–(A1) is synthesized by a stoichiometric controlled Stille cross-coupling-reaction of donor carbazole 5(b/c) with 4,7-dibromobenzo[ c ][1,2,5]thiadiazole 10 (Scheme ) to yield (D)–(S)–(A1) 11a and 11b .…”

Section: Resultsmentioning

confidence: 99%

“…13 C NMR gave signals at 1.2 (grease) ppm . Tetrakis(triphenylphosphine)palladium(0), tributyl(3-methylthiophene-2-yl)stannane ( 3 ), 4,7-dibromobenzo[ c ][1,2,5]thiadiazole ( 10 ), 3,6-dibromo-9 H -carbazole ( 1 ), 5-(7-bromobenzo[ c ][1,2,5]thiadiazol-4-yl)thiophene-2-carbaldehyde ( 8 ), 3,3′-diiodo-2,2′-dimethoxy-1,1′-binaphthalene ( 13( S )a ), and 2,2′-dimethoxy-1,1′-binaphthalene ( 12( S ) ) were synthesized according to the reported literature. 3-Iodo-2,2′-dimethoxy-1,1′-binaphthalene ( 13( S )b ) was synthesized in a modified synthetic procedure of the reported literature in improved yields …”

Section: Methodsmentioning

confidence: 99%

Synthesis of Chiral Donor–Acceptor Dyes to Study Electron Transfer Across a Chiral Bridge

2020

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Chiral organic dyes comprising a donor (D), spacer (S), primary acceptor (A1), chiral bridge (B(S)), and final acceptor/radical (A2)/(R) have been synthesized and fully characterized. The goal behind this synthetic pursuit is to study whether the chiral dyes can impart a chiral-induced spin selectivity (CISS) spin-filtering effect during an intramolecular charge-transfer (CT) process. Additionally, appending a stable free radical (SFR) allows the study of how an unpaired spin influences the CT state. The dyes are reported to vary in the position of (A1) with respect to (B(S)). Two series of dyes have been synthesized: one series incorporates (A1) before (B(S)) and the second series places (A1) after (B(S)). In the case where (A1) is before (B(S)), CT is observed between (D) and (A1), but the CT state does not transverse over the chiral bridge to the final (A2)/(R) termini. However, when (A1) is placed after (B(S)), CT over or through the bridge occurs. Computations support the experimental data, which indicate that it is necessary to have (A1) located after (B(S)) to achieve CT over the chiral bridge. Hence, the second set of dyes are optimal candidates to explore intramolecular CISS.

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Supramolecular interactions of fluorene-based copolymers containing 3,4-propylenedioxythiophene and phenazine units with SWNTs

Abstract: Interaction of an electron-rich ProDOT-containing conjugated polymer and an electron poor phenazine-containing conjugated polymer with single-walled carbon nanotubes exhibits some selectivity for metallic vs. semiconducting structures.

Cited by 11 publications

References 78 publications

Helical Conjugated Ladder Polymers: Tuning the Conformation and Properties through Edge Design

Helical Conjugated Ladder Polymers: Tuning the Conformation and Properties through Edge Design

Understanding Noncovalent Interactions of Small Molecules with Carbon Nanotubes

Synthesis of Chiral Donor–Acceptor Dyes to Study Electron Transfer Across a Chiral Bridge

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