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Title: Poly(naphthalene diimide) vinylene: solid state red emission and semiconducting properties for transistors

Abstract

Here in this work, a conjugated polymer PNV is developed, linking naphthalene diimide with a vinyl linkage. Owing to the C-H ∙∙∙O hydrogen bond between the carbonyl and the vinyl, PNV exhibits a high red emission with a quantum yield of 33.4% in the solid state while it shows n-type properties with an electron mobility up to 1.5 x 10 -3 cm 2 V -1 s -1 in organic field effect transistors, simultaneously.

Authors:
 [1]; ORCiD logo [2]; ORCiD logo [3];  [3];  [3];  [4];  [2];  [2];  [5]; ORCiD logo [6]
  1. Chongqing Univ. (China). School of Chemistry and Chemical Engineering; Yunnan Minzu Univ., Kunming (China). YMU-HKBU Joint Lab. of Traditional Natural Medicine
  2. Chongqing Univ. (China). School of Chemistry and Chemical Engineering
  3. Chinese Academy of Sciences (CAS), Beijing (China). Inst. of Chemistry. Beijing National Lab. for Molecular Sciences
  4. Yunnan Minzu Univ., Kunming (China). YMU-HKBU Joint Lab. of Traditional Natural Medicine
  5. Chinese Academy of Sciences (CAS), Chongqing (China). Chongqing Inst. of Green and Intelligent Technology
  6. Argonne National Lab. (ANL), Argonne, IL (United States). Materials Science Division; Univ. of Chicago, IL (United States). Inst. for Molecular Engineering
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22); National Natural Science Foundation of China (NNSFC); Chinese Academy of Sciences (CAS)
OSTI Identifier:
1364439
Grant/Contract Number:
AC02-06CH11357
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
ChemComm
Additional Journal Information:
Journal Volume: 53; Journal Issue: 36; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Liang, Xianfeng, Tan, Luxi, Liu, Zitong, Ma, Yanping, Zhang, Guanxin, Wang, Lin, Li, Shayu, Dong, Lichun, Li, Jing, and Chen, Wei. Poly(naphthalene diimide) vinylene: solid state red emission and semiconducting properties for transistors. United States: N. p., 2017. Web. doi:10.1039/C7CC01372H.
Liang, Xianfeng, Tan, Luxi, Liu, Zitong, Ma, Yanping, Zhang, Guanxin, Wang, Lin, Li, Shayu, Dong, Lichun, Li, Jing, & Chen, Wei. Poly(naphthalene diimide) vinylene: solid state red emission and semiconducting properties for transistors. United States. doi:10.1039/C7CC01372H.
Liang, Xianfeng, Tan, Luxi, Liu, Zitong, Ma, Yanping, Zhang, Guanxin, Wang, Lin, Li, Shayu, Dong, Lichun, Li, Jing, and Chen, Wei. Thu . "Poly(naphthalene diimide) vinylene: solid state red emission and semiconducting properties for transistors". United States. doi:10.1039/C7CC01372H. https://www.osti.gov/servlets/purl/1364439.
@article{osti_1364439,
title = {Poly(naphthalene diimide) vinylene: solid state red emission and semiconducting properties for transistors},
author = {Liang, Xianfeng and Tan, Luxi and Liu, Zitong and Ma, Yanping and Zhang, Guanxin and Wang, Lin and Li, Shayu and Dong, Lichun and Li, Jing and Chen, Wei},
abstractNote = {Here in this work, a conjugated polymer PNV is developed, linking naphthalene diimide with a vinyl linkage. Owing to the C-H ∙∙∙O hydrogen bond between the carbonyl and the vinyl, PNV exhibits a high red emission with a quantum yield of 33.4% in the solid state while it shows n-type properties with an electron mobility up to 1.5 x 10-3 cm2 V-1 s-1 in organic field effect transistors, simultaneously.},
doi = {10.1039/C7CC01372H},
journal = {ChemComm},
number = 36,
volume = 53,
place = {United States},
year = {Thu Apr 06 00:00:00 EDT 2017},
month = {Thu Apr 06 00:00:00 EDT 2017}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 2works
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  • We present measurements of the optical absorption and emission properties of poly({ital p}-phenylene vinylene) (PPV) -related materials focusing on the differences between molecules isolated by dispersion in an inert host and concentrated molecular films. Optical absorption spectra, photoluminescence (PL) spectra, PL efficiency, and time-resolved PL spectra of dilute blends of PPV oligomers with 2{endash}5 phenylene-phenyl rings are compared with those of dense oligomer and polymer films. In dilute oligomer-poly(methyl methacrylate) (PMMA) blends with high PL efficiency, the PL decay is exponential, independent of both temperature and oligomer length. This implies that the fundamental radiative lifetime of PPV oligomers is essentiallymore » independent of oligomer length. Concentrated spin-cast oligomer films and polymers have a faster and strongly temperature-dependent PL decay that approaches that of the dilute oligomer results at low temperature. The differences in PL decay correspond to changes in PL efficiency. The efficiency of the oligomer-PMMA blend is high and only weakly temperature dependent, whereas that of concentrated films is lower and strongly temperature dependent, decreasing by more than a factor of 3 from 10 to 350 K. The quenching of the PL efficiency in concentrated films is due to migration to extrinsic, impurity related centers as opposed to an intrinsic intermolecular recombination process. The PL spectrum of a dilute oligomer blend redshifts substantially, both as the excitation energy is decreased and as the emission time increases. This spectral redshift is due to disorder-induced site-to-site variation and not to diffusion to lower-energy sites. In contrast, no spectral shift with excitation energy or emission time was observed for dense oligomer films. {copyright} {ital 1996 The American Physical Society.}« less
  • Self assembling {pi}-conjugated molecules into ordered structures are of increasing interest in the field of organic electronics. One particular example is charge transfer complexes containing columnar alternative donor-acceptor (ADA) stacks, where neutral and ionic ground states can be readily tuned to modulate electrical, optical, and ferroelectrical properties. Aromatic-aromatic and charge transfer interactions have been the leading driving forces in assisting the self-assembly of ADA stacks. Various folding structures containing ADA stacks were assembled in solution with the aid of solvophobic or ion-binding interactions. Meanwhile, examples of solid ADA stacks, which are more appealing for practical use in devices, were obtainedmore » from cocrystalization of binary components or mesophase assembly of liquid crystals in bulk blends. Regardless of these examples, faster and more controllable approaches towards precise supramolecular order in the solid state are still highly desirable.« less
  • The naphthalene-1,4:5,8-bis(dicarboximide) radical anion (NDI -˙), which is easily produced by mild chemical or electrochemical reduction (-0.5 Vvs.SCE), can be photoexcited at wavelengths as long as 785 nm, and has an excited state (NDI -˙*) oxidation potential of -2.1 Vvs.SCE, making it a very attractive choice for artificial photosynthetic systems that require powerful photoreductants, such as CO 2 reduction catalysts. However, once an electron is transferred from NDI -˙* to an acceptor directly bound to it, a combination of strong electronic coupling and favorable free energy change frequently make the back electron transfer rapid. To mitigate this effect, we havemore » designed a molecular triad system comprising an NDI -˙ chromophoric donor, a 9,10-diphenylanthracene (DPA) intermediate acceptor, and a Re(dmb)(CO) 3carbon dioxide reduction catalyst, where dmb is 4,4'-dimethyl-2,2'-bipyridine, as the terminal acceptor. Photoexcitation of NDI -˙ to NDI -˙* is followed by ultrafast reduction of DPA to DPA -˙, which then rapidly reduces the metal complex. The overall time constant for the forward electron transfer to reduce the metal complex is τ = 20.8 ps, while the time constant for back-electron transfer is six orders of magnitude longer, τ = 43.4 μs. Achieving long-lived, highly reduced states of these metal complexes is a necessary condition for their use as catalysts. The extremely long lifetime of the reduced metal complex is attributed to careful tuning of the redox potentials of the chromophore and intermediate acceptor. The NDI -˙–DPA fragment presents many attractive features for incorporation into other photoinduced electron transfer assemblies directed at the long-lived photosensitization of difficult-to-reduce catalytic centers.« less
  • Solid-state [sup 13]C cross-polarization magic-angle-spinning (CPMAS) nuclear magnetic resonance (NMR) spectra have been obtained for films of poly (p-phenylene vinylene) (PPV) and PPV-d[sub 4], poly (p-2,3,5,6-tetradeutero-phenylene vinylene). All four phenylene and vinylene resonance have been assigned. The [sup 13]C CPMAS NMR spectra show the presence of phenylene ring 180[degrees] rotation jumps. Solid-state [sup 2]H quadrupole-echo nuclear magnetic resonance spectra of PPV-d[sub 4] films show that all the phenylene rings of PPV undergo 180[degrees] rotational jumps about the 1,4 ring axis with a median activation energy of 15 kcal/mo. The effects of concentrated sulfurice acid doping of PPV-d[sub 4] have beenmore » examined with [sup 2]H quadrupole echo NMR spectroscopy. Stretched PPV films have been prepared in which the vinylene protons have been substituted with deuterium (PPV-d[sub 2]). [sup 2]H spectra of aligned samples at high temperature show molecular motion. [sup 2]H quadrupole echo NMR spectra of oriented PPV-d[sub 4] aligned in the NMR magnetic field have been simulated and have yielded the chain orientation distribution in these films. [sup 2]H spectra obtained at [minus]58[degrees]C are well simulated by an orientation distribution consisting of two Gaussian components. PPV has been doped with sodium metal. The chemistry of this process has been examined with elemental analysis. ESR spectroscopy has followed the evolution of unpaired spins as the doping reaction proceeds. Two-dimensional [sup 13]C-[sup 1]H HETCOR CP-MAS NMR spectra of p-dimethoxybenzene (DMB) and poly(2,5-dimethoxy-p-phenylene vinylene) (PDMPV) with variable [sup 1]H dipolar mixing times have been analyzed to determine the rates of [sup 1]H magnetization transfer between chemically distinct protons. Internuclear distances have been obtained from these rates and the conformation of the PDMPV repeat unit has been calculated and discussed.« less