Time-Dependent Solid-State Polymorphism of a Series of Donor–Acceptor Dyads

Peebles, Cameron; Alvey, Paul M.; Lynch, Vincent M.; Iverson, Brent L.

doi:10.1021/cg401522v

Cited by 15 publications

(26 citation statements)

References 51 publications

(151 reference statements)

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“…As indicated recently by Iverson et al [20], there are numerous aromatic donor -aromatic acceptor systems exhibiting highly directional interactions between the peripheral groups rather than the alternating aromatic donor -aromatic acceptor stacking.…”

Section: Page 4 Of 31mentioning

confidence: 87%

WITHDRAWN: Hydrogen-bonding versus π–π stacking in the design of organic semiconductors: From dyes to oligomers

Gospodinova¹,

Tomšík²

2014

Progress in Polymer Science

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This review discusses some general aspects of the highly directional intermolecular interactions in organic solids, followed by an overview of π-conjugated systems exhibiting directional preference in the intermolecular connection and demonstrating enhanced energy and/or charge carrier transfer. As examples, "small" dyes and pigments, "intermediate-sized" N-heteroacenes, and "large" hydrogen-bonded oligomers are considered. In all of these systems the intermolecular interactions between polarized peripheries of the π-conjugated moieties ensure a preferential direction in the molecular packing. The most important among these interactions are hydrogen bonds (both strong and weak). As demonstrated recently, hydrogen bonding represents a dominant attractive force even for molecules with different polarization of the π-conjugated aromatic or heterocyclic moieties, considered to be the most favorable condition for "face-to-face" orientation (π−π stacking).The solid-state anisotropy, most likely, results from the nematic liquid-crystalline ordering of both thermotropic and lyotropic origin. Moreover, the unique efficiency of the exciton diffusion in the J-aggregates of dyes indicates significant potential of the nematic liquidcrystalline state itself for the design of organic semiconductors.

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Section: Page 4 Of 31mentioning

confidence: 87%

WITHDRAWN: Hydrogen-bonding versus π–π stacking in the design of organic semiconductors: From dyes to oligomers

Gospodinova¹,

Tomšík²

2014

Progress in Polymer Science

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“…1c). 29 Orange crystals of dyad 4, referred to as 4s from now on, produced upon slower evaporation (more than 10 days) from 1 : 1 : 1 DCM : MeOH : acetone displayed an orange-red emission (Fig. 1f) and were also found to contain a head-to-head (NI-NI) stacking geometry similar to that seen in the yellow-orange 1s crystal (Fig.…”

Section: Introductionmentioning

confidence: 88%

“…1a). 29 Dyad 1 was found to form two distinct and differently colored crystal forms as a function of crystal growth time: a yellow head-to-tail (NI-MAN aromatic interaction) crystal with green emission after faster evaporation (1f, 1-2 days) from chloroform (Fig. 1b) and a yellow-orange head-to-head (NI-NI aromatic interaction) crystal with orange emission after slower evaporation (1s, more than 5 days) from 1 : 1 : 1 toluene : MeOH : ethyl acetate (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…However, based on powder XRD data, it was proposed that both 2 and 3 were stacked in a head-to-tail fashion in the solids that formed. Based on XRD patterns and modeling we proposed that 4f is also packed in a 29 and schematic packing of slower evaporated 1f observed to stack in a head-to-tail orientation. (c) Crystal structure and schematic packing of faster evaporated 1s observed to stack in a head-to-head orientation.…”

Section: Introductionmentioning

confidence: 99%

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Solution- and solid-state photophysical and stimuli-responsive behavior in conjugated monoalkoxynaphthalene–naphthalimide donor–acceptor dyads

2015

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The stimuli--responsive properties of a series of aromatic conjugated monoalkoxynaphthalene--naphthalimide donor--acceptor dyads were studied. Two of the dyads, dyads 1 and 4, showed a difference in solid--state color between relatively faster (yellow) and slower (yellow--orange or orange) evaporation from solution, while the other dyads, dyad 2 and 3, only showed one color (yellow--green) for both evaporation rates. Importantly, highly solvatochromic dyad 4 dis-played thermochromic (orange to yellow), mechanochromic (orange to yellow) and vapochromic (yellow to orange) stim-uli--responsive behavior in the solid--state with repeatable cycles of color changing. Structural and spectroscopic studies indicated that the stimuli--responsive behavior of dyad 4 is the result of a 180° molecular rotation wherein the thermody-namically more stable head--to--head stacked orange crystalline solid interconverts with a head--to--tail stacked soft-crystalline yellow mesophase. The thermochromic transition of 4 from a presumably more stable crystalline state (or-ange) to a metastable soft crystalline mesophase state (yellow) that persists at room temperature unless exposed to sol-vent vapor is particularly noteworthy.

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“…A monomer, 6-methoxy-2-ethynylnaphthalene (6MeO2EN), was prepared as described in the literature [36]. The monomers, 7-methoxy-2-ethynylnaphthalene (7MeO2EN) and 8-methoxy-2-ethynylnaphthalene (8MeO2EN), were prepared as described in Scheme S1 (Supplementary Materials) and purified by column chromatography on silica gel with n -hexane prior to use.…”

Section: Methodsmentioning

confidence: 99%

Methoxy-Group Control of Helical Pitch in Stereoregular Poly(2-ethynylmethoxynaphthalene) Prepared by Rhodium Complex Catalyst

Mawatari

Yoshida

Huang³

et al. 2019

Polymers

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The position of the methoxy group in a poly(n-methoxy-2-ethynylnaphthalene) (PnMeO2EN) was found to control the helical pitch of the π-conjugated polymer in the solid state. These PnMeO2ENs were stereoregularly synthesized using an Rh-complex catalyst in ethanol or toluene as the solvent. The helical structure in the solid phase was confirmed by conventional analytical methods, namely diffuse reflective ultraviolet–visible light (UV–Vis) and Raman spectroscopies, X-ray diffraction, and 13C cross-polarization magic angle spinning NMR spectroscopy, together with molecular mechanics calculations, because the as obtained polymers were insoluble in common solvents. The color of poly(6-methoxy-2-ethynylnaphthalene) (P6MeO2EN) (yellow or red) depended on the polymerization solvent, whereas no such dependency was observed for the yellow-colored P7MeO2EN and P8MeO2EN. The helical structures energetically optimized by molecular mechanics indicate that the red- and yellow-colored P6MeO2ENs form contracted and stretched helices, respectively. Due to the relatively unconstrained rotations of the 6-methoxynaphthyl moieties, the methoxy groups in P6MeO2EN are less sterically hindered along the helical axis. On the contrary, P7MeO2EN and P8MeO2EN have stretched helices due to the considerable steric hindrance imparted by their methoxy groups. The thermal cis-to-trans isomerization of P6MeO2EN in the contracted-helix form required a somewhat higher temperature than that of the stretched helix.

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Time-Dependent Solid-State Polymorphism of a Series of Donor–Acceptor Dyads

Cited by 15 publications

References 51 publications

WITHDRAWN: Hydrogen-bonding versus π–π stacking in the design of organic semiconductors: From dyes to oligomers

WITHDRAWN: Hydrogen-bonding versus π–π stacking in the design of organic semiconductors: From dyes to oligomers

Solution- and solid-state photophysical and stimuli-responsive behavior in conjugated monoalkoxynaphthalene–naphthalimide donor–acceptor dyads

Methoxy-Group Control of Helical Pitch in Stereoregular Poly(2-ethynylmethoxynaphthalene) Prepared by Rhodium Complex Catalyst

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