Printing technology based on isotropic liquid phase of naphthalene diimide derivatives for n-type organic transistors

Synthesis, Solution, and Solid State Properties of Homological Dialkylated Naphthalene Diimides—A Systematic Review of Molecules for Next-Generation Organic Electronics

“…The solubility of NDIs in cyclohexane, n-hexane, or n-heptane is significantly lower. In our study, we tested and verified the solubility of NDIs in solvents commonly used in the fabrication of organic electronic films [ 5 , 51 , 53 ]. The solubility of NDIs was, therefore, tested in chloroform, 1,2-dichlorobenzene, and toluene—good solvents for NDIs, as well as n-heptane—a poor solvent [ 49 , 53 , 54 ].…”

“…In our study, we tested and verified the solubility of NDIs in solvents commonly used in the fabrication of organic electronic films [ 5 , 51 , 53 ]. The solubility of NDIs was, therefore, tested in chloroform, 1,2-dichlorobenzene, and toluene—good solvents for NDIs, as well as n-heptane—a poor solvent [ 49 , 53 , 54 ]. Our solubility tests indicated that the solubility of NDIC5 through NDIC8 and of NDIC10 in chloroform exceeded 100 mg/mL.…”

“…The solubility of the NDIC3, NDIC4, NDIC9, and NDIC11 in chloroform was 46.9 ± 1.5, 65.5 ± 1.6, 47 ± 1.0, and 15.15 ± 0.6 mg/mL, respectively. Considering applications of NDIs in, for instance, printed organic electronics, that solubility in the case of all NDIs exceeds usual needs since typically used concentrations oscillate within 2–20 mg/mL [ 5 , 51 , 53 ]. Conversely, the solubility of NDIs in n-heptane ( Figure 3 and Table S4 ) was two orders of magnitude lower than in chloroform.…”

Nature of the N‐Substituted Alkyl Chain Influencing Emission Properties of Naphthalene Diimide (NDI) Via Excimer, and Exciplex Formation

“…In this realm, the substituted n-type naphthalene diimide (NDI) derivatives and their self-assembled structures; such as fluorescent organic nanoparticle (FONPs), [6,7] LMW gels, [8,9] vesicles, [10,11] and other supramolecular structures have been used in different applications including sensing, [12,13] as a drug, [14] for bioimaging, [15] and in organic electronics. [16,17] The main challenge associated with NDI derivative is the poor optical properties [18] when modified at the imide position which limits their applications compared to a similar class of πaromatic compounds such as perylene diimide (PDI) which shows excellent quantum yield values near to unity. [19] Many of the literature reports suggest various strategies to overcome this limitation mainly by structural modification and also adapting suitable methods of self-assembly such as aggregation in the solvent mixture, [20] excimer/exiplex formation, [21,22] aggregation-induced enhanced emission (AIEE), [23] donor-acceptor (DÀ A) interactions, [24] and H-/J-type aggregate formation, [25] etc.…”

“…Self‐assembly [1,2] is a technique by which wide varieties of supramolecular architectures [3] are generated, particularly from the low molecular weight (LMW) [4,5] organic entities. In this realm, the substituted n‐type naphthalene diimide (NDI) derivatives and their self‐assembled structures; such as fluorescent organic nanoparticle (FONPs), [6,7] LMW gels, [8,9] vesicles, [10,11] and other supramolecular structures have been used in different applications including sensing, [12,13] as a drug, [14] for bioimaging, [15] and in organic electronics [16,17] . The main challenge associated with NDI derivative is the poor optical properties [18] when modified at the imide position which limits their applications compared to a similar class of π ‐aromatic compounds such as perylene diimide (PDI) which shows excellent quantum yield values near to unity [19] .…”