Chapter 1. Supramolecular Chemistry of Naphthalenediimide and its Congeners

Prentice, Giles M.; Emmett, Liam; Luxami, Vijay; Pantoş, G. Dan

doi:10.1039/9781782621386-00001

Cited by 4 publications

(15 citation statements)

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“…The planar aromatic system of NDIs is responsible for aromatic π-stacking and Van der Waals interactions with other aromatic species. In fact, most aromatic rings present a quadrupole moment created by their electron density with a partial negative charge above and below the face and a partial positive charge around the periphery ( Prentice et al, 2017 ).…”

Section: Bioimaging Methods and Biosensing Tools For Detecting Prosta...mentioning

confidence: 99%

Nano-Theranostics for the Sensing, Imaging and Therapy of Prostate Cancers

et al. 2022

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We highlight hereby recent developments in the emerging field of theranostics, which encompasses the combination of therapeutics and diagnostics in a single entity aimed for an early-stage diagnosis, image-guided therapy as well as evaluation of therapeutic outcomes of relevance to prostate cancer (PCa). Prostate cancer is one of the most common malignancies in men and a frequent cause of male cancer death. As such, this overview is concerned with recent developments in imaging and sensing of relevance to prostate cancer diagnosis and therapeutic monitoring. A major advantage for the effective treatment of PCa is an early diagnosis that would provide information for an appropriate treatment. Several imaging techniques are being developed to diagnose and monitor different stages of cancer in general, and patient stratification is particularly relevant for PCa. Hybrid imaging techniques applicable for diagnosis combine complementary structural and morphological information to enhance resolution and sensitivity of imaging. The focus of this review is to sum up some of the most recent advances in the nanotechnological approaches to the sensing and treatment of prostate cancer (PCa). Targeted imaging using nanoparticles, radiotracers and biomarkers could result to a more specialised and personalised diagnosis and treatment of PCa. A myriad of reports has been published literature proposing methods to detect and treat PCa using nanoparticles but the number of techniques approved for clinical use is relatively small. Another facet of this report is on reviewing aspects of the role of functional nanoparticles in multimodality imaging therapy considering recent developments in simultaneous PET-MRI (Positron Emission Tomography-Magnetic Resonance Imaging) coupled with optical imaging in vitro and in vivo, whilst highlighting feasible case studies that hold promise for the next generation of dual modality medical imaging of PCa. It is envisaged that progress in the field of imaging and sensing domains, taken together, could benefit from the biomedical implementation of new synthetic platforms such as metal complexes and functional materials supported on organic molecular species, which can be conjugated to targeting biomolecules and encompass adaptable and versatile molecular architectures. Furthermore, we include hereby an overview of aspects of biosensing methods aimed to tackle PCa: prostate biomarkers such as Prostate Specific Antigen (PSA) have been incorporated into synthetic platforms and explored in the context of sensing and imaging applications in preclinical investigations for the early detection of PCa. Finally, some of the societal concerns around nanotechnology being used for the detection of PCa are considered and addressed together with the concerns about the toxicity of nanoparticles–these were aspects of recent lively debates that currently hamper the clinical advancements of nano-theranostics. The publications survey conducted for this review includes, to the best of our knowledge, some of the most recent relevant literature examples from the state-of-the-art. Highlighting these advances would be of interest to the biomedical research community aiming to advance the application of theranostics particularly in PCa diagnosis and treatment, but also to those interested in the development of new probes and methodologies for the simultaneous imaging and therapy monitoring employed for PCa targeting.

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Section: Bioimaging Methods and Biosensing Tools For Detecting Prosta...mentioning

confidence: 99%

Nano-Theranostics for the Sensing, Imaging and Therapy of Prostate Cancers

et al. 2022

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“…Consequently, both ordered and disordered layers are attributed to double-layer structures. Hence, the intermolecular interactions, in this case presumably face-to-face π-aggregation, 25,28 are significantly stronger than the BNTCDI/Au(111) interfacial interactions. Consequently, molecular double layers are formed almost exclusively even in the case of submonolayer coverage.…”

Section: Resultsmentioning

confidence: 98%

“…6,17 This is possible as a result of the electron withdrawing nature of the imide group producing a partial positive charge on the aromatic C−Hs. 25 The formation of the C(sp 2 )−H•••imide oxygen hydrogen bonds between neighboring NDI backbones together with the space requirements of the substituents at the nitrogen atoms define the geometry and usually result in the displacement (D x ) of adjacent molecule pairs along the long molecular axes. These hydrogen bonds are marked exemplarily by gray dotted lines in the schematic illustration of Figure 2a.…”

Section: Resultsmentioning

confidence: 99%

“…NDIs, in general, are prototypical molecules for the forming of supramolecular networks. In disubstituted NDIs, like BNTCDI, the formation of N–H···O hydrogen bonds is not possible, but they are able to form nonclassical intermolecular C–H···O hydrogen bonds. , This is possible as a result of the electron withdrawing nature of the imide group producing a partial positive charge on the aromatic C–Hs . The formation of the C(sp 2 )–H···imide oxygen hydrogen bonds between neighboring NDI backbones together with the space requirements of the substituents at the nitrogen atoms define the geometry and usually result in the displacement ( D x ) of adjacent molecule pairs along the long molecular axes.…”

Section: Resultsmentioning

confidence: 99%

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Complex Adsorption Behavior of a Nonplanar Naphthalene Diimide on Au(111)

et al. 2019

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Naphthalene diimide (NDI) derivatives are extensively studied in the field of supramolecular and materials chemistry due to their versatility in coordination, electron deficiency, and planar aromatic core. Here, we report on the self-assembly behavior and the electronic properties of 2,7dibenzyl-1,4,5,8-naphthalenetetracarboxylic diimide (BNTCDI) studied by low-temperature scanning tunneling microscopy. BNTCDI adsorbed on Au(111) is highly mobile and reveals a tendency to form chain structures on the step edges at low coverages. The chains are kept together by intermolecular hydrogen bonds between neighboring NDI backbones. Within the chain structures, the orbital appearance of single molecules was clearly identified. Additionally, supramolecular structures consisting of ordered double layers were observed on terraces for higher surface coverages. The molecule−substrate interaction is investigated in detail via scanning tunneling spectroscopy for different molecular arrangements. The results reveal distinct insights into the subtle balance between intermolecular and interface interactions determining the self-assembly behavior of BNTCDI resulting in chain structures at step edges and ordered double layers on Au(111) terraces.

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“…This atom-economical hydroamination of NDIs possesses unique characteristics that are distinctively different from other existing chemical reactions for π-systems: (1) various amines, many of which are commercially available, are applicable to functionalize the π-systems, and thus (2) the π-conjugated structure is changed by the reaction to exhibit remarkable changes in the optical and electronic properties. In this context, considering that NDIs have been widely known as building blocks of supramolecular polymers, 42–45 we conceived that our catalyst-free hydroamination of NDIs could be used as a new family of in situ reactions to trigger macroscopic changes of supramolecular polymers based on NDI molecules using various amines. The in situ reaction of π-conjugated molecules within supramolecular polymers is also expected to exhibit characteristic reactivity different from that in homogeneous monodisperse solutions, because the molecules are pre-organized and locally condensed.…”

Section: Introductionmentioning

confidence: 99%