RESUMEN
Quinolines and quinoline-containing macromolecules are renowned for their valuable biological activities and excellent materials properties. Herein, we validate a general strategy for the synthesis of chloro-containing quinoline, benzoquinoline and polybenzoquinoline variants via the aza-Diels-Alder reaction. The described findings could be ultimately implemented in other synthetic pathways and may open new opportunities for analogous quinoline-derived materials.
RESUMEN
Naturally occurring and recombinant protein-based materials are frequently employed for the study of fundamental biological processes and are often leveraged for applications in areas as diverse as electronics, optics, bioengineering, medicine, and even fashion. Within this context, unique structural proteins known as reflectins have recently attracted substantial attention due to their key roles in the fascinating color-changing capabilities of cephalopods and their technological potential as biophotonic and bioelectronic materials. However, progress toward understanding reflectins has been hindered by their atypical aromatic and charged residue-enriched sequences, extreme sensitivities to subtle changes in environmental conditions, and well-known propensities for aggregation. Herein, we elucidate the structure of a reflectin variant at the molecular level, demonstrate a straightforward mechanical agitation-based methodology for controlling this variant's hierarchical assembly, and establish a direct correlation between the protein's structural characteristics and intrinsic optical properties. Altogether, our findings address multiple challenges associated with the development of reflectins as materials, furnish molecular-level insight into the mechanistic underpinnings of cephalopod skin cells' color-changing functionalities, and may inform new research directions across biochemistry, cellular biology, bioengineering, and optics.
RESUMEN
This study describes the synthesis of modular diquinolineanthracene and polydiquinolineanthracene derivatives. The reported facile and scalable aza-Diels-Alder-based approach requires mild conditions, proceeds in two steps, uses commercially available starting materials, and accommodates varying functionalities. Given the known utility of the acene and quinoline motifs, the synthesized molecules and polymers hold promise for organic electronics applications.
RESUMEN
Graphene nanoribbons (GNRs) are promising candidate materials for the next generation of nanoscale electronics. Described herein is the synthesis of 2,4,6-substituted benzoquinolines, which constitute building blocks for nitrogen-doped GNRs. The presented facile and modular aza-Diels-Alder chemistry accommodates the installation of diverse functionalities at the crowded benzoquinolines' 2 positions. Given the general utility of the benzoquinoline motif, these findings hold relevance not only for carbon-based electronics but also for a range of chemical disciplines.
RESUMEN
Graphene nanoribbons (GNRs) represent promising materials for the next generation of nanoscale electronics. However, despite substantial progress towards the bottom-up synthesis of chemically and structurally well-defined all-carbon GNRs, strategies for the preparation of their nitrogen-doped analogs remain at a nascent stage. This scarce literature precedent is surprising given the established use of substitutional doping for tuning the properties of electronic materials. Herein, we report the synthesis of a previously unknown class of polybenzoquinoline-based materials, which have potential as GNR precursors. Our scalable and facile approach employs few synthetic steps, inexpensive commercial starting materials, and straightforward reaction conditions. Moreover, due to the importance of quinoline derivatives for a variety of applications, the reported findings may hold implications across a diverse range of chemical and physical disciplines.
