From linear to cyclic oligoparaphenylenes: electronic and molecular changes traced in the vibrational Raman spectra and reformulation of the bond length alternation pattern
Literature Information
Lili Qiu, Mercedes Taravillo, Valentín G. Baonza, M. Carmen Ruiz Delgado, Shigeru Yamago, Ramesh Jasti, Juan T. López Navarrete, Juan Casado, Miklos Kertesz
Cyclic paraphenylenes, [n]CPPs, and linear paraphenylenes, [n]LPPs, formed by n benzenes, are investigated by Raman spectroscopy for n = 5 to 12 and density functional theory (DFT) for n = 4 to 20. The information on the experimental Raman frequencies and intensities, combined with DFT computations and reported X-ray diffraction structures, provides a consistent interpretation of the Raman spectra and allows establishing relevant structure–property trends. Structural and electronic effects such as benzene ring bending, inter-ring torsions, π-conjugation (aromaticity) and orbital energy gaps as a function of the linear elongation in [n]LPPs versus the macrocyclic curvature in [n]CPPs and of the molecular size (i.e., polymer limit) are systematically analyzed on the basis of the vibrational Raman properties. Changes in the BLA as an indicator of the degree of quinonoid character are analyzed and linked to the Effective Conjugation Coordinate (ECC) model. The BLA patterns involved in twisted and non-twisted conformations and in different species (bipolarons, quinonoid tautomers, and ECC active modes) are compared and their differences are discussed. This paper offers a unified interpretation of structural and electronic aspects in relation to the evolution from linear 1D π-systems to cyclic 2D structures.
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Source Journal
Physical Chemistry Chemical Physics

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.
![[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-(2,2,2-trichloroethoxycarbonyloxy)propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate structure [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-(2,2,2-trichloroethoxycarbonyloxy)propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate structure](https://static.chemtradehub.com/structs/100/100431-55-8-7104.webp)



