Design and synthesis of trithiophene-bound excited-state intramolecular proton transfer dye: enhancement on the performance of bulk heterojunction solar cells.

In an aim to harvest UV-near-visible (360-440 nm) photons as well as to increase the morphology in the bulk heterojunction solar cells, we report herein the strategic design, synthesis, and characterization of a novel excited-state intramolecular proton-transfer dye, 3-hydroxy-2-(5-(5-(5-(3-hydroxy-4-oxo-4H-chromen-2-yl)thiophen-2-yl)thiophen-2-yl)thiophen-2-yl)-4H-chromen-4-one (FT), which bears two key functional groups, namely 3-hydroxychromone chromophore and trithiophene backbone and is then exploited into the blends of regioregular poly(3-hexylthiophene) (RR-P3HT) and phenyl-C(61)-butyric acid methyl ester (PCBM). FT acts as an excellent UV-near visible absorber, which then undergoes excited-state intramolecular proton transfer, giving rise to an orange-red proton-transfer emission that was reabsorbed by P3HT via a Forster type of energy transfer. Introduction of FT to P3HT/PCBM blend films also improves the morphology of phase separated structure, in particular, enhances the interaction of P3HT chains and the hole mobility. In this work, under the optimized condition of P3HT: PCBM:FT of 15:9:2 in weight ratio, the best performance of the device B-FT2 revealed consistent enhancements in the efficiency (eta) 4.28% and short-circuit current (J(sc)) 12.53 mAcm(-2), which are higher than that (3.68% and 10.28 mAcm(-2)) of the best performance of the control device B (P3HT:PCBM 15:9 in weight ratio) by 16 and 22%, respectively.

7-Azamelatonin: efficient synthetic routes, excited-state double proton transfer properties and biomedical implications.

On the basis of a seven-step synthetic route, the total synthesis of 7-azamelatonin, an analogue of melatonin, has been achieved with an overall yield of approximately 9.2%. In aqueous solution, 7-azamelatonin exhibits a unique excited-state double proton transfer (ESDPT) property, resulting in dual emission bands (405 and 560 nm). The ESDPT property makes 7-azamelatonin superb as a potential molecular probe for future bioapplication and for pharmacological research.

Synthesis of 7-azaserotonin: its photophysical properties associated with excited state proton transfer reaction.

We report the synthesis of 3-(2-aminoethyl)-5-ol-1H-pyrrolo[2,3-b]pyridine (7-azaserotonin), which may potentially serve as an agonist or antagonist of serotonin receptors. In alcohols, the solvent (e.g., ethanol) catalyzed proton-transfer reaction takes place for 7-azaserotonin in the excited state, resulting in dual emission. Conversely, excited-state deprotonation takes place in neutral aqueous solution. The unique excitation behavior makes 7-azaserotonin versatile as a potential bioprobe.