Exploring the potential of anthracene derivatives as fluorescence emitters for biomedical applications

Abstract

Two novel anthracene derivatives were synthesized, detailed photo-physical and biological investigations were carried out utilizing variety of spectroscopy techniques. The effect of cyano (-CN) substitution was found effective to alter...

Pore-Confined π-Chromophoric Tetracene as a Visible Light Harvester toward MOF-Based Photocatalytic CO2 Reduction in Water

“…Integrating light-harvesting transition metal complexes, particularly Ir– and Ru–polypyridyl complexes, is well established and attributes the excellent light-harvesting property to otherwise feebly absorbing pristine MOFs. − In addition, inorganic semiconductors (e.g., TiO 2 ), plasmonic metal nanoparticles (e.g., Ag), and quantum dots (e.g., CsPbBr 3 ) are also incorporated with MOFs for enhancing their visible light absorption. − However, exploring the light-harvesting capability of the conjugated π-chromophoric class of molecules such as acene in photocatalytic reactions is yet to be investigated. Basically, acenes are a series of π-chromophoric polycyclic aromatic compounds comprising linearly fused benzene rings, which can possess highly intense absorption and emission properties and have attracted significant importance in the field of organic optoelectronic including the improvement in solar cell efficiency. − Moreover, these polyacenes, especially tetracene and pentacene, are known for possessing singlet fission due to their comparable energy level of the lowest singlet energy state and triplet pair . However, exploring their light-harvesting ability to benefit the photoinduced energy and electron transfer processes for chemical transformation is in its infancy.…”

Achieving beyond 100% Triplet State Generation with Singlet Fission Strategy for High-Performance Photosensitizer Design

“…Anthracene, first discovered in coal tar by Dumas and Laurent in 1832, possessing the advantages of high fluorescence quantum yield, superb charge-carrier transport properties, and simple synthesis route, has been widely used in optoelectronic devices, imaging, and therapeutics. − For instance, the famed 1 O 2 probes singlet oxygen sensor green (SOSG) and 9,10-anthracenediyl-bis­(methylene)­dimalonic acid (ABDA) are based on the specific reaction between anthracenes and 1 O 2 to form endoperoxides (EPOs) with distinct optical property changes, , while their reversible reaction has been employed in 1 O 2 delivery for oxygen-independent PDT. − In addition, planar anthracene was also used to design PSs based on the SOCT-ISC mechanism. , On the other hand, several anthracenes have also been reported with a unique property of singlet fission (SF) in thin films. − SF process occurs between a S 1 fluorophore and a S 0 fluorophore, which converts one S 1 into a distinct intermediate 1 (TT), followed by triplet-pair separation into two T 1 fluorophores, with the theoretical T 1 generation yield of 200% . SF requires the S 1 energy level to be no less than 2-fold of T 1 energy level (i.e., E (S 1 ) ≥ 2 E (T 1 )), and appropriate electronic coupling for 1 (TT) intermediate formation and triplet-pair separation (Scheme ).…”

Formation of Highly Emissive Anthracene Excimers for Aggregation-Induced Emission/Self-Assembly Directed (Bio)imaging

“…Among the myriad of AIEgens, anthracene and its derivatives have been extensively investigated for applications in material science based on their excellent luminescence properties due to the formation of different supramolecular structures that range from linear dimers to π–π stacking arrangement of the anthracene units. − Thus, several attempts have been made to use anthracene derivatives in the biomedical field, encompassing anticancer drug design, biosensing, cross-linkers, hybrid materials, and others. − From all the possible supramolecular arrangements that anthracene and its derivatives may adopt, the unusual T-shaped geometry is the most sought after due to its excellent luminescence properties. − However, its formation in a biological environment has never been described. We recently reported on a new anthracene-guanidine derivative (AG) that is able to form the rare T-shaped dimer in aqueous solution where the water molecules play a fundamental role in assisting the self-assembly process through H-bonds.…”