Double intramolecular hydrogen transfer assisted dual emission in a carbazole-embedded porphyrin-like macrocycle

Abstract

Introduction of pyrrole ring at one of the meso positions of the carbazole-based porphyrins lowers the structural symmetry and exhibits dual emission, which strongly depends on the excitation wavelength and...

Stable Inner 2H Tautomer of N-Confused-like Porphyrin Embedded with a Carbazole Subunit: Synthesis, Metal Coordination, and Magnetic and Anion Sensing Studies

“…The identified opposite signature suggests the diamagnetic or paramagnetic nature of the metal cations. The positive NICS(1) value could be due to the induced paratropic ring current from Cu(II), which is analogous to a recent report on dihydrodiazatrioxa [9]circulene. 54 Such a change in the sign of NICS(1) values is presumably originating from the metal center rather than the macrocyclic ligand effect (Figure S8 Using NH-carbz as reference, ϕ F = 28.9 in toluene.…”

“…Notably, the fluorescence of 1 shows a gradual shift upon increasing the solvent polarity from nhexane to ethanol due to its stabilized excited state (Figure S5−5). 9 Upon addition of F − , the disappearance of the NH signal at 8.43 ppm was observed (Figure S3−7). However, further increasing the concentration of F − did not show the NH deprotonated byproduct, suggesting poor stability of the FHF − anion in less polar solvent.…”

“…The structural modification of the π-conjugated porphyrin core has progressed significantly in various research fields such as catalysis, 1 sensors, 2 organic electronics, 3 nonlinear optics, 4 and photodynamic therapy. 5 In the past decade, several research groups developed the synthesis of carbazole-based porphyrinoids and studied their unique metal coordination ability, 6 switchable near-IR absorption, 7 redox interconversion, 8 dual emission, 9 strong excitonic coupling, 10 and photoacoustic imaging applications. 11 The unique photophysical properties of porphyrin analogues can be utilized as chemosensors.…”

Carbazole-embedded p-benziporphyrinoid: synthesis, structure and a reversible chemodosimeter for mercury(ii) ions

“…Recently our group has reported various carbazole-based macrocycles exhibiting dual-emissive and excitonically coupled chromophores. 18,19 Subsequently, we have also demonstrated a carbazole-embedded furan-containing macrocycle that showed distinct and reversible mercury binding (F). 4 On the contrary, an inverted pyrrole-containing carbazole-embedded macrocycle selectively binds toxic F À and CN À ions.…”