Amphoteric tetrazole-substituted eleven-ring-fused acene derivatives with multiple fluorescent protonation states.

We synthesized novel tetrazole-substituted diacenaphthoanthracenediimides 2 by azide cycloaddition to the corresponding cyano-substituted precursors. Reversible protonation/deprotonation of the tetrazole moieties provides distinct fluorescent species with photoluminescence quantum yields of 12-34%. The facile deprotonation of 2 enables its processing in non-halogenated solvents (alcohol).

Long-range hydrogen-bond relay catalyses the excited-state proton transfer reaction.

Solvent (, water)-catalyzed proton transfer (SCPT) the relay of hydrogen (H)-bonds plays a key role in proton migration. In this study, a new class of 1-pyrrolo[3,2-]quinolines (PyrQs) and their derivatives were synthesized, with sufficient separation of the pyrrolic proton donating and pyridinic proton accepting sites to probe excited-state SCPT. There was dual fluorescence for all PyrQs in methanol, , normal (PyrQ) and tautomer 8-pyrrolo[3,2]quinoline (8H-PyrQ) emissions.

Tandem Desulfurization/C-C Coupling Reaction of Tetrathienylbenzenes on Cu(111): Synthesis of Pentacene and an Exotic Ladder Polymer.

Surface-confined reactions represent a powerful approach for the precise synthesis of low-dimensional organic materials. A complete understanding of the pathways of surface reactions would enable the rational synthesis of a wide range of molecules and polymers. Here, we report different reaction pathways of tetrathienylbenzene (T1TB) and its extended congener tetrakis(dithienyl)benzene (T2TB) on Cu(111), investigated using scanning tunneling microscopy, X-ray photoelectron spectroscopy, and density functional theory calculations.

Catalytic-Type Excited-State N-H Proton-Transfer Reaction in 7-Aminoquinoline and Its Derivatives.

7-Aminoquinoline (7AQ) and various amino derivatives thereof (-NHR) have been strategically designed and synthesized to study their excited-state proton-transfer (ESPT) properties. Due to the large separation between the proton donor -NHR and the acceptor -N- site, ESPT in 7AQ derivatives, if available, should proceed under protic solvent catalysis. ESPT is found to be influenced by the acidity of -NHR and the basicity of the proton-acceptor -N- in the quinoline moiety.