Development of Imidazo[1,2- a]pyridine Derivatives with an Intramolecular Hydrogen-Bonded Seven-Membered Ring Exhibiting Bright ESIPT Luminescence in the Solid State.

Org Lett

Department of Materials and Environmental Science, Institute of Industrial Science , The University of Tokyo, 4-6-1, Komaba , Meguro-ku, Tokyo 153-8505 , Japan.

Published: April 2019

Imidazo[1,2- a]pyridine derivatives with different hydroxyaryl units (1-3), which could potentially form an intramolecular hydrogen-bonded seven-membered ring in either a planar or a twisted conformation, were newly developed, and the effect of conformation and steric repulsion on the excited-state intramolecular proton transfer (ESIPT) luminescence was evaluated. Among them, 1 and 2 formed an intramolecular hydrogen-bonded seven-membered ring in the crystalline state and exhibited efficient ESIPT luminescence in the solid state (quantum yield up to 0.45).

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.9b00455DOI Listing

Publication Analysis

Top Keywords

intramolecular hydrogen-bonded
12
hydrogen-bonded seven-membered
12
seven-membered ring
12
esipt luminescence
12
imidazo[12- a]pyridine
8
a]pyridine derivatives
8
luminescence solid
8
solid state
8
development imidazo[12-
4
intramolecular
4

Similar Publications

Selective Self-Assembly of Supramolecular Helices and Macrocycles Directed by Halogen Bonding.

Chemistry

December 2024

Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.

In this study, several hydrogen-bonded arylamide foldamers (compounds 1-5) with the same degree of polymerization were designed and synthesized. The polyfluoroiodobenzene or iodoethynyl polyfluoroiodobenzene segment was modified as a halogen donor at the end of the monomer, and pyridine or pyridine oxynitride served as the corresponding halogen acceptor segment. The crystal structure of compound 1 indicates that the supramolecular double helices were constructed by stacking a P helix and an M helix in an antiparallel manner in the direction of intermolecular I⋅⋅⋅O-N halogen bonding.

View Article and Find Full Text PDF

The coupled structural and electronic parameters of intramolecular hydrogen bonding play an important role in ultrafast chemical reactions, such as proton transfer processes. We perform one- and two-dimensional vibrational-electronic (1D and 2D VE) spectroscopy experiments to understand the couplings between vibrational and electronic coordinates in 10-Hydroxybenzo[h]quinoline, an ultrafast proton transfer system. The experiments reveal that the OH stretch (νOH) is strongly coupled to the electronic excitation, and Fourier analysis of the 1D data shows coherent oscillations from the low frequency backbone vibrational modes coupled to the νOH mode, resulting in an electronically detected vibronic signal.

View Article and Find Full Text PDF

Water interfaces play a crucial role in regulating interactions and energy flow. Vibrational sum-frequency generation (vSFG) spectroscopy provides structural and dynamic information on water molecules at interfaces. It has revealed, for instance, the presence of the hydrogen-bonded and free OH groups at the air-water interface.

View Article and Find Full Text PDF

Heterochiral coupling to bilateral β-turn structured azapeptides bearing two remote chiral centers.

Nat Commun

October 2024

MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.

Enantioselective synthesis governed by chiral catalysts has been extensively developed, but that without any chiral auxiliaries or chiral catalysts is rare, particularly when remote stereogenic centers are involved. Here we report an enantioselectivity of heterochiral coupling in the one-pot reaction of racemic hydrazides with achiral 1,4-bis(isothiocyanine)benzene, yielding preferentially the heterochiral bilateral azapeptides over the homochiral ones. Despite bearing two hydrogen-bonded β-turn structures that allow intramolecular chiral transfer, the bilateral azapeptide products have two chiral centers separated by 14 atoms or 15 bonds, which prevent the direct intramolecular asymmetric communication between the two chiral centers.

View Article and Find Full Text PDF

Photoexcitation Dynamics of 4-Aminopthalimide in Solution Investigated Using Femtosecond Time-Resolved Infrared Spectroscopy.

Int J Mol Sci

October 2024

Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.

Excited-state intramolecular proton transfer (ESIPT) reactions are crucial in photoresponsive materials and fluorescent markers. The fluorescent compound 4-aminophthalimide (4-AP) has been reported to exhibit solvent-assisted ESIPT in protic solvents, such as methanol, wherein the solvent interacts with 4-AP to form a six-membered hydrogen-bonded ring that is strengthened upon excitation. Although the controversial observation of ESIPT in 4-AP has been extensively studied, the molecular mechanism has yet to be fully explored.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!