Paracyclophanes as model compounds for strongly interacting π-systems. Part 1. Pseudo-ortho-dihydroxy[2.2]paracyclophane

Literature Information

Publication Date 2010-06-29
DOI 10.1039/B925634B
Impact Factor 3.676
Authors

Conrad Kaiser


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Abstract

In this work we describe a study of the ground and first excited state structures and energetics of a dihydroxy-derivative of [2.2]paracyclophane (PC), the pseudo-ortho-dihydroxy[2.2]paracyclophane (o-DHPC), also termed 4,12-dihydroxy[2.2]paracyclophane. In order to understand the electronic interactions between the two π-systems, the molecule is investigated by REMPI spectroscopy in a free jet and by quantum chemical calculations. REMPI-spectra of the cluster with one water molecule were also obtained and aid in the interpretation. The origin of the S1 ← S0 transition lies at 31 483 cm−1 (3.903 eV) for o-DHPC and 31 263 cm−1 (3.876 eV) for the o-DHPC·H2O cluster. An adiabatic excitation energy of 3.87 eV was computed for the S1 ← S0 transition in o-DHPC. The SCS-CC2 calculations deviate by less than 0.1 eV for the adiabatic excitation energies of PC, o-DHPC and the related aromatic molecules benzene and phenol. Considerable activity in a breathing vibration of 190 cm−1 is found in the S1 state of o-DHPC and o-DHPC·H2O, in agreement with the computed SCS-CC2 value of 185 cm−1. Further vibrations appear at +11 cm−1 and +54 cm−1 in o-DHPC. The computations and the available experimental data of the parent PC show that both PC and o-DHPC are rather flexible with respect to motions of the benzene moieties. While PC has a double minimum potential energy with respect to the torsional motion, a single-minimum structure is found for the ground state of o-DHPC. The geometry change upon excitation is less pronounced in o-DHPC as compared to PC. Two of the three possible rotational conformers of the OH groups were found to have similar energies, but spectral hole burning shows that the spectra are dominated by a single rotamer.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
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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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