Good conductivity of a single component polydiacetylene film

Tang, Zhen‐Yu; Li, Ming; Song, Miao; Jiang, Li; Li, Jinhua; He, Yunbin; Zhou, Ling

doi:10.1016/j.orgel.2017.06.058

Cited by 10 publications

(5 citation statements)

References 18 publications

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“…While some natural furan-based diacetylene (DA) do exist [38][39][40], no attempts to polymerize them have been reported. This seems quite surprising since polydiacetylene (PDA) has attracted tremendous attention for applications in various fields [41,42] due to its unique chromatic [43][44][45][46][47][48][49][50] and semi-conductive properties [51][52][53][54][55][56][57][58][59][60][61].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

et al. 2019

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Crystal structure elucidations of bio-based polymers provide invaluable data regarding structure-property relationships. In this work, we achieved synthesis and Single Crystal X-ray Diffraction (SCXRD) structural determination of a new furan-based polydiacetylene (PDA) derivative with carbamate (urethane) functionality. Firstly, diacetylene (DA) monomers were found to self-assemble in the crystalline state in such a way that the polymerization theoretically occurred in two different directions. Indeed, for both directions, geometrical parameters for the reactive alignment of DA are satisfied and closely related with the optimal geometrical parameters for DA topochemical polymerization (d(1) = 4.7-5.2 Å, d(2) ≤ 3.8 Å, θ ≈ 45 • ). However, within the axis of hydrogen bonds (HB), the self-assembling monomers display distances and angles (d(1) = 4.816 Å, d(2) = 3.822 Å, θ = 51 • ) that deviate more from the ideal values than those in the perpendicular direction (d(1) = 4.915Å, d(2) = 3.499Å, θ ≈ 45 • ). As expected from these observations, the thermal topochemical polymerization occurs in the direction perpendicular to the HB and the resulting PDA was characterized by SCXRD.

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Section: Introductionmentioning

confidence: 99%

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

et al. 2019

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“… 33 After irradiation, peaks of P 4 disappeared but a broad region (355–500 cm –1 ) referring to poly-phosphorus appeared, 34 while there was no visible peak referring to the P–C bond, 35 indicating that all P 4 has converted to poly-phosphorus. The typical peak of a pillar unit (diacetylene) at 2253 cm –1 remained in all spectra 36 of the MOF, MOF@P 4 and irradiated MOF@P 4 . The C 1s envelope in XPS measurements reveals that all peaks referring to C C, C C, C–C, C–O and COO remained the same with no new peaks referring to the P–C bond (ESI Fig.…”

Section: Resultsmentioning

confidence: 93%

Synthesis of a 2D phosphorus material in a MOF-based 2D nano-reactor

Liu

et al. 2018

Chem. Sci.

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“…Before iodine treatment and after removal of iodine, the conductivities of C 12 O-1 and PC 12 O-1 at room temperature were on the order of 10 –8 –10 –7 S m –1 . Since the conductivities of pristine PDAs are reported to be on the order of 10 –14 –10 –7 S m –1 , − those of C 12 O-1 and PC 12 O-1 are within the range but are relatively high. During iodine doping, the conductivities of C 12 O-1 and PC 12 O-1 increased, and they were finally saturated at 8.4 × 10 –5 and 1.2 × 10 –2 S m –1 , respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Solid-State Polymerization of 5-(Pyren-1-yl)penta-2,4-diyn-1-ol Derivatives with an N-Phenylurethane or N-Benzylurethane Group

Oshimizu

Takeshi

Sato

et al. 2020

Crystal Growth & Design

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A series of 5-(pyren-1-yl)penta-2,4-diyn-1-yl N-phenylcarbamates and N-benzylcarbamates were synthesized. Phenyl groups in the N-phenyl and N-benzyl moieties were unsubstituted (H-0 and H-1, respectively) and 3,4,5-trialkoxy substituted (C m O-0 and C m O-1, respectively), in which the alkyl groups introduced were methyl (m = 1), octyl (m = 8), dodecyl (m = 12), and hexadecyl (m = 16) groups. Upon UV irradiation, a regular 1,4-addition polymerization to form polydiacetylene was confirmed for H-0, H-1, C 8 O-1, C 12 O-1, and C 16 O-1. For C 1 O-0 and C 1 O-1, the crystal structures were solved, and the reasons the regular polymerization did not occur were clarified. From the powder X-ray diffraction study, crystallinities of C m O-1 were found to be lower than those of C m O-0, although C m O-1 regularly polymerized. This indicates that the total crystallinity is not directly related to local ordering around one-dimensional arrays for the polymerization direction. Polymerized C m O-1 species were soluble in chloroform. Their processability enabled us to fabricate cast films of polydiacetylene as well as the monomer. The conductivities of C 12 O-1 and the polymer (PC 12 O-1) were evaluated in the pristine and iodine-doped states and in the charge-transfer-complexed states with 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane. A conductivity of 1.2 × 10 −2 S m −1 for iodine-doped PC 12 O-1 was achieved. In this case, pyrene moieties seemed to play an important role in realizing the appropriate electron transfer from pyrene moieties to iodine molecules and effective π conjugation between the pyrene moieties and the PDA backbone promoting charge transport.

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Good conductivity of a single component polydiacetylene film

Cited by 10 publications

References 18 publications

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

Preparation and Single Crystal Structure Determination of the First Biobased Furan-Polydiacetylene Using Topochemical Polymerization

Synthesis of a 2D phosphorus material in a MOF-based 2D nano-reactor

Synthesis and Solid-State Polymerization of 5-(Pyren-1-yl)penta-2,4-diyn-1-ol Derivatives with an N-Phenylurethane or N-Benzylurethane Group

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