title: Efficient Synthesis and Photosensitizer Performance of Nonplanar Organic Donor-Acceptor Molecules.
abstract: Nonplanar organic donor-acceptor molecules bearing a carboxylic acid group were synthesized by the formal [2+2] cycloaddition-retroelectrocyclization reaction between aniline-substituted alkynes and tetracyanoethylene (TCNE) or 7,7,8,8-tetracyanoquinodimethane (TCNQ). This reaction offers an atom-economic one-step approach to donor-acceptor chromophores in satisfactory high yields. The resulting donor-acceptor molecules were characterized by conventional analytical techniques. In addition, the nonplanarity and intermolecular interactions were investigated by X-ray crystallography. The energy levels and intramolecular charge-transfer (CT), evaluated by UV-Vis-near IR spectroscopy and electrochemistry, suggested that there is a linear correlation between the optical and electrochemical band gaps. Based on these structural and electronic analyses, the photosensitizer performances of the donor-acceptor molecules in dye-sensitized solar cells (DSSCs) were initially investigated using TiO2 or SnO2 electrodes. Although the power conversion efficiencies were limited, the incident-photon-to-current-conversion efficiency (IPCE) spectra indicated a better photocurrent generation for the devices on SnO2 as compared to those on TiO2.
authors.forename: Yuping
authors.initials: Y
authors.lastname: Yuan
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Michinobu
authors.forename: Norifusa
authors.initials: N
authors.lastname: Satoh
authors.forename: Minoru
authors.initials: M
authors.lastname: Ashizawa
authors.forename: Liyuan
authors.initials: L
authors.lastname: Han
mesh_terms: D004396:Coloring Agents / Q000138:chemical synthesis* / Q000528:radiation effects; D003198:Computer Simulation; D003460:Crystallization / Q000379:methods; D004579:Electron Transport / Q000528:radiation effects; D005030:Ethylenes / Q000737:chemistry* / Q000528:radiation effects; D008027:Light; D008422:Materials Testing; D008956:Models, Chemical; D008958:Models, Molecular; D009570:Nitriles / Q000737:chemistry* / Q000528:radiation effects; D010316:Particle Size; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000528:radiation effects
chemical_list: D004396:Coloring Agents; D005030:Ethylenes; D009570:Nitriles; D017319:Photosensitizing Agents; C013703:tetracyanoquinodimethane; C003393:tetracyanoethylene