A study of the competitive multiple hydrogen bonding effect and its associated excited-state proton transfer tautomerism

Literature Information

Publication Date 2017-10-03
DOI 10.1039/C7CP05002J
Impact Factor 3.676
Authors

Yi-Ting Chen, Pei-Jhen Wu, Chia-Yu Peng, Jiun-Yi Shen, Cheng-Cheng Tsai, Wei-Ping Hu, Pi-Tai Chou


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Abstract

1,8-Dihydroxynaphthalene-2,7-dicarbaldehyde (DHDA) has been strategically designed and synthesized with the aim to study the competitive multiple hydrogen bonding (H-bonding) effect and the associated excited-state intramolecular proton transfer reaction (ESIPT). In nonpolar solvents such as cyclohexane, equilibrium exists between the two H-bonding isomers DHDA-23_OO and DHDA-23_OI, both of which possess double intramolecular H-bonds. In polar, aprotic solvents such as CH2Cl2, DHDA-23_OO becomes the predominant species. Due to various degrees of H-bond induced changes of electronic configuration each isomer reveals a distinct absorption feature and excited-state behavior, in which DHDA-23_OI in cyclohexane undergoes double ESIPT in a stepwise manner, giving the first and second proton-transfer tautomer emissions maximized at ∼500 nm and 660 nm, respectively. As for DHDA-23_OO both single and double ESIPT are prohibited, resulting in an intense normal 450 nm emission band. In a single crystal DHDA-23_OI is the dominant species, which undergoes excited state double proton transfer, giving intense emission bands at 530 nm and 650 nm. The mechanism associated with competitive multiple H-bonding energetics and ESIPT was underpinned by detailed spectroscopy/dynamics and computational approaches.

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Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

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