23536-15-4Relevant articles and documents
1,4;5,8-naphthalene-tetracarboxylic diimide derivatives as model compounds for molecular layer epitaxy
Ofir, Yuval,Zelichenok, Alexander,Yitzchaik, Shlomo
, p. 2142 - 2149 (2006)
The physical properties and finite size effects observed in 1,4;5,8-naphthalene-tetracarboxylicdiimide (NTCDI)-based organic multilayers assembled by molecular layer epitaxy (MLE) are investigated by structure-property studies of low molecular weight mode
Tunable columnar mesophases utilizing C2 symmetric aromatic donor-acceptor complexes
Reczek, Joseph J.,Villazor, Karen R.,Lynch, Vincent,Swager, Timothy M.,Iverson, Brent L.
, p. 7995 - 8002 (2006)
Derivatives of relatively electron rich 1,5-dialkoxynaphthalene (Dan) donors and relatively electron deficient 1,4,5,8-naphthalenetetracarboxylic diimide (Ndi) acceptors have been exploited in the folding and self-assembly of a variety of complex molecular systems in solution. Here, we report the use of Dan and Ndi derivatives to direct assembly of extended columns with alternating face-centered stacked structure in the solid state. A variety of 1:1 Dan:Ndi mixtures produced mesophases that were found to be stable over temperature ranges extending up to 110 °C. Analysis of these mesophases indicates mixtures with soft/plastic crystal phases and a few mixtures with the thermodynamic properties of true liquid crystals, all composed of alternating donor-acceptor columns within. Importantly, a correspondence was found between the clearing and crystallization points of the mesophase mixtures and the melting/clearing points of the component Ndi and Dan units, respectively. This correspondence enables the predictable tuning of mesophase phase transition temperatures. The study of sterically hindered derivatives led to a set of mixtures in which a dramatic and sudden color change (deep red to yellow) was observed upon crystallization of the mesophase due to a phase separation of the component donor and acceptor units.
Organic radical compound and carbon nanotube composites with enhanced electrical conductivity towards high-performance p-type and n-type thermoelectric materials
Chen, Zhanhua,Huang, Hongfeng,Liu, Danqing,Wang, Dagang,Wang, Lei,Wang, Yanzhao
, p. 24675 - 24684 (2020)
Small organic molecules are promising as the next generation of thermoelectric materials due to their unique advantages, such as low cost, high mechanical flexibility, low thermal conductivity, and low toxicity. However, their low electrical conductivities seriously limit the realization of high power factors. Herein, naphthalene diimide derivatives (NDI-1 and NDI-2) carrying a radical substituent of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are designed and complexed with single-walled carbon nanotubes (SWCNTs) as both p-type and n-type thermoelectric composites. The introduction of the radical substituent remarkably improved the electrical conductivity by almost fifty percent compared to that of the NDI derivative without the radical substituent (NDI-0). The obtained radical-containing composites display greatly enhanced TE performance with highest power factors of 277.1 ± 5.4 μW m-1 K-2 for the p-type composite and 79.6 ± 1.7 μW m-1 K-2 for the n-type composite, respectively. Furthermore, the thermoelectric module based on NDI-1/SWCNT composite films consisting of five p-n junctions reaches a large output power of 2.81 μW under a 65 K temperature gradient. The enhanced electrical conductivities and TE performances of radical-containing NDI/SWCNT composite films are attributable to the improved doping level and charge transport process between the radical molecules and SWCNTs. This design strategy of introducing radical moieties into organic thermoelectric materials might be beneficial to the future application for high-performance p-type and n-type thermoelectric materials and devices. This journal is
Appending Diverse π-Extended Acceptors with Tetrathiafulvalene/Dithiafulvalene Donors: Multistate Redox Properties, Radical Ion Generation, and Mid-IR-Absorbing Mixed-Valence States
Keshri, Sudhir Kumar,Asthana, Deepak,Chorol, Sonam,Kumar, Yogendra,Mukhopadhyay, Pritam
, p. 1821 - 1832 (2018)
Three classes of donor–acceptor (D–A) π-extended chromophores (1–12) were synthesized through a phosphite-mediated cross-coupling reaction, in which the anhydride- or imide-based π-As and number of tetrathiafulvalene (TTF)/dithiafulvalene (DTF) Ds were systematically changed. Large π rings, such as benzoperylene and coronene, were integrated into the TTF/DTF unit, for the first time, to overcome their high insolubility. The anhydride and imide groups in the π acceptors can significantly alter the frontier orbitals and influence the optoelectronic properties. The D moieties allow the formation of radical cations (D.+) and the π-extended A moieties aid the formation of radical anions (A.?) by oxidation/reduction under ambient conditions. The molecules revealed UV/Vis/near-IR absorption, fluorescence extending into the near-IR region, and amphoteric electrochemical properties. Chromophores 10 and 12 show solvatochromism in a wide range of solvents. The π-As with anhydride functionality allow easier electron uptake, relative to the imide groups, whereas the increasing number of D TTF/DTF units make them easy to oxidize. Interestingly, the trans-TTF-fused molecules (1, 6, and 11) exhibited a mixed-valence state in the mid-IR region ((Formula presented.) =5130–4000 cm?1). Moderate electron coupling between the redox centers is inferred to the compounds being of Robin–Day class II. The multistate redox activity along with panchromism and near-/mid-IR optical absorption of these systems can be attractive towards advanced switchable materials.
Polymorphism in: N, N ′-dialkyl-naphthalene diimides
Cavallini, Massimiliano,Cowen, Lewis,Degousée, Thibault,Drain, Ben A.,Fenwick, Oliver,Guagliardi, Antonietta,Liscio, Fabiola,Luong, Sally,Masciocchi, Norberto,Milita, Silvia,Schroeder, Bob C.
, p. 3097 - 3112 (2020)
The long-known class of compounds called naphthalene diimides (NDI), bearing alkyl substituents on the imide nitrogen atoms, have been widely used as active materials in thin film devices with interesting optical, sensing and electrical applications. Less is known about their rich crystal chemical behaviour, which comprises numerous polymorphic transitions, and the appearance of elusive liquid crystalline phases. It is this behaviour which determines the response of the devices based on them. Here we fully characterized, by combining differential scanning calorimetry, powder and thin film diffraction and optical microscopy techniques, two newly synthesized NDI materials bearing n-octyl and n-decyl side-chains, as well as lighter analogues, of known room temperature crystal structures. In search for a rationale of their physico-chemical properties, phase stability and thermally induced solid-state transition reversibility, the differential behaviour of these NDI materials is interpreted here based on the competitive role of intermolecular π-π interactions and the alkyl chain flexibility. The appearance of comparable local minima of the molecular conformational energy hypersurface for shorter alkyls, and, for longer ones, of rotator phases, is here invoked.
Naphthalene diimide based materials with adjustable redox potentials: Evaluation for organic lithium-ion batteries
Vadehra, Geeta S.,Maloney, Ryan P.,Garcia-Garibay, Miguel A.,Dunn, Bruce
, p. 7151 - 7157 (2015/02/19)
The promising crystallinity and tunable redox capabilities of naphthalene diimides make them attractive candidates as electroactive materials for organic-based lithium-ion batteries. In this study, a family of naphthalene diimide derivates was synthesized and their redox properties explored with the intent of unveiling structures with reduction potentials that are higher than those encountered in previous organic redox processes. Changes in the electronic characteristics of the aryl substituents resulted in materials with discharge potentials that vary from 2.3 to 2.9 V vs Li/Li+, with discharge capacities as high as 121 mAh/g.
Synthesis of macrocycles and an unusually asymmetric [2]catenane via templated acetylenic couplings
Hamilton, Darren G.,Prodi, Luca,Feeder, Neil,Sanders, Jeremy K. M.
, p. 1057 - 1065 (2007/10/03)
An unusually asymmetric [2]catenane has been prepared by interlocking a hybrid crown macrocycle (containing one polyether and one butadiyne linker) with a diimide-derived macrocycle itself constructed with a pair of rigid butadiyne links. This system of complementary building blocks and connectors has proved a versatile vehicle for demonstration of a number of templating effects. Synthesis of the hybrid crown monomer by intramolecular cyclisation is promoted by the presence of a benzene diimide, acting as a positive template, but a sufficiently different effect is exerted by a naphthalene diimide derivative that intermolecular dimerisation becomes significant. Templating the hybrid crown synthesis with an 'active' benzene diimide, itself bearing acetylene functions, allows the first tandem synthesis of a catenane comprising two different rings: the diimide first acts as a template for the formation of the hybrid crown, which itself in turn acts as a template for cyclodimerisation of the acetylenic diimide. Remarkably, the yield of catenane is essentially independent of the initial cyclisation state of the crown component. No significant production of covalently linked donor-acceptor species is observed from these reactions, supporting the presence of an intermediate complex pre-organised to catenane formation. In contrast, oxidative coupling of an alkyl solubilised diimide gave no interlocked products and yielded only small amounts of cyclic poly-imide macrocyles.
