34151-51-4

Upstream product

• 3731-53-1 4-(aminomethyl)pyridine 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 5690-24-4 1,4,5,8-naphthalenetetracaraboxylic dianhydride 

Relevant academic research and scientific papers

Electronic, optical, and computational studies of a redox-active napthalenediimide-based coordination polymer

The new one-dimensional coordination framework (Zn(DMF)NO3) 2(NDC)(DPMNI), where NDC = 2,6-naphthalenedicarboxylate and DPMNI = N,N′-bis(4-pyridylmethyl)-1,4,5,8-naphthalenetetracarboxydiimide, which has been crystallographically characterized, exhibits two redox-accessible states due to the successive reduction of the naphthalenediimide (NDI) ligand core. Solid-state electrochemical and vis-near-IR spectroelectrochemical measurements coupled with density functional theory (DFT) calculations enabled the origins of the optical transitions in the spectra of the monoradical anion and dianion states of the material to be assigned. Electron paramagnetic resonance (EPR) spectroscopy revealed that the paramagnetic radical anion state of the DPMNI core could be accessed upon broad-spectrum white light irradiation of the material, revealing a long-lived excited state, possibly stabilized by charge delocalization which arises from extensive π-π* stacking interactions between alternating NDC and NDI aromatic cores which are separated by a distance of 3.580(2) A.

Structural tuning of coordination polymers by 4-connecting metal node and secondary building process

Five transition metal coordination polymers, {[Cu(4-pmntd)2(NO3)2]?2CHCl3}n (1), {[Cu(4-pmntd)2(NO3)2]·3C7H8}n (2), {[Cu(4-pmntd)

Co(II)-based Metal-Organic Frameworks and Their Application in Gas Sorption and Solvatochromism

We report the synthesis and structural characterization of a unique Co-MOF-1 with the formula [Co2(dpmndi)(bdc)2)]·DMF; (dpmndi = N,N′-bis(4-pyridylmethyl)-1,4,5,8-naphthalenediimide and bdc = benzene-1,4-dicarboxylate) along with an

A Boat-Shaped Tetracationic Macrocycle with a Semiconducting Organic Framework

We report the synthesis of a tetracationic macrocycle which contains two N,N′-bis(methylene)naphthalenediimide units inserted in between the pyridinium rings of the bipyridinium units in cyclobis(paraquat-p-phenylene) (CBPQT4+ or “blue box”) an

Supramolecular structural transformation of: N, N ′-bis(4-pyridylmethyl)-naphthalene diimide and fluorescence water sensing

A supramolecular structure based on N,N′-bis(4-pyridylmethyl)-naphthalene diimide exhibits reversible phase transitions in a single-crystal-to-single-crystal process. Such temperature induced SC-SC transformations are driven by intermolecular π-π interactions and hydrogen bond interaction. Interestingly, the dynamic supramolecular structure shows selective adsorption and fluorescence water sensing.

Photoinduced electron transfer in N,N-bis(pyridylmethyl)naphthalenediimides: study of their potential as pH chemosensors

The change in fluorescent properties of a series of N,N-bis(pyridylmethyl)naphthalenediimides (BIPy-NDIs) as function of pH were investigated. The naphthalenediimide dyes displayed OFF–ON pH sensing properties owing to photoinduced electron transfer in the pH range from 1.7 to 4.1. The fluorescence enhancement of the chemosensors studied is based on the hindering of photoinduced energy-electron transfer (PET) from pyridine ring to the naphthalene fluorophore by protonation. Moreover, using density functional theory theoretical calculations of molecular orbitals, it was verified that protonation nitrogen atom in pyridine ring inhibits the PET process. The best selective response for monitoring pH in the presence of different metal ions, was exhibited by BIPy-NDI 1B. In addition, 1B was applied for determination of pH in real samples of commercial vinegars. The results were consistent with those obtained by glass electrode method, indicating that the new probe could be a practical pH indicator in strongly acidic conditions.

Self-stacking of naphthalene bis(dicarboximide)s probed by NMR

The self-stacking in water of a series of naphthalene-1,8:4,5-bis(dicarboximide)s (also known as naphthalene diimides, NDIs) bearing cationic side chains has been studied using NMR techniques. The position of the charge in the side chain has a strong effect on the propensity of the NDI to self-stack. Examples with a cationic center three atoms away from the NDI ring in general do not self-stack; those with cationic centers further out on the side chains are prone to self-stack at NMR concentrations. The size of the side chain per se does not appear to be a significant controlling factor; even a derivative with biotin side chains shows no evidence of self-stacking. Increasing the ionic strength of the solution can also induce stacking. Derivatives with aromatic side chains can show intramolecular self-stacking of the side chain with the central NDI ring. This is significant for side chains with isoquinoline and bipyridine groups but not significant for side chains with pyridine groups. An example of an NDI that undergoes both intramolecular and intermolecular stacking is the derivative bearing side chains ending in Ru(bpy),2+3 moieties. In methanol, the shift patterns of the aromatic resonances of the bipyridine rings are very close to those of a model compound. However, a more complicated chemical shift pattern is seen in water. This indicates that conformations with the Ru(bpy),2+3 moieties lying at least partly within the shielding cone of the aromatic NDI system are favored. Molecular modeling indicates that conformations in which the bipyridine ring interacts with the NDI ring are readily-achievable. The temperature dependence of the chemical shifts for this molecule indicates that both intramolecular interactions of the bipyridine rings with the NDI ring and self-stacking of the NDI rings are significant.