Isophlorin derivatives: Structures and materials for n-Channel Organic Semiconductors

Issue title: Atomic and molecular nonlinear optics: Theory, Experiment and Computation A homage to the pioneering work of Stanisław Kielich (1925-1993)

Guest editors: G. Maroulis, T. Bancewicz, B. Champagne and A.D. Buckingham

Article type: Research Article

Authors: Jissy, A.K. | Datta, Ayan^{; *}

Affiliations: School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, CET Campus, Thiruvananthapuram – 695016, Kerala, India

Correspondence: [*] Corresponding author. E-mail: ayan@iisertvm.ac.in.

Abstract: DFT and NMR calculations performed on isophlorin (1) and their derivatives (2–10) show that the 4O and the trans 2O, 2S derivatives (2 and 5) are anti-aromatic. The presence of strong S…S pπ-pπ bonding interactions stabilizes the planar structure (5) compared to the non-planar cis-isomer (8). Isophlorins are predicted to have very low electron reorganization energies (λelectron∼0.10eV) which remain unaffected by puckering through steric interactions or solvation in aqueous media. We predict isophlorins to be the ideal candidates for n-Channel organic conductors.

DOI: 10.3233/JCM-2010-0319

Journal: Journal of Computational Methods in Sciences and Engineering, vol. 10, no. 3-6, pp. 203-218, 2010