PMID- 25323762 OWN - NLM STAT- PubMed-not-MEDLINE DCOM- 20150521 LR - 20141128 IS - 1521-3765 (Electronic) IS - 0947-6539 (Linking) VI - 20 IP - 50 DP - 2014 Dec 8 TI - Regioisomeric effects on the electronic features of indenothiophene-bridged D-pi-A'-A DSSC sensitizers. PG - 16574-82 LID - 10.1002/chem.201403584 [doi] AB - Two D-pi-A'-A regioisomers (A-IDT-D and D-IDT-A) featuring 4,4'-di-p-tolyl-4 H-indeno[1,2-b]-thiophene as a pi linker (pi) between the diarylamino donor (D) and the pyrimidine-cyanoacrylic acid acceptor (A'-A) have been successfully synthesized and characterized as efficient sensitizers for the dye-sensitized solar cells (DSSCs). The different arrangements of the D and A'-A blocks on the unsymmetrical indenothiophene (IDT) core render the dipole of IDT being along (A-IDT-D) or opposite (D-IDT-A) to the direction of intramolecular (donor-to-acceptor) charge transfer, and thus induce variations in the physical properties. The experimental observations correlated well with the theoretical analyses, clearly revealing the trade-off between the molar extinction coefficient (epsilon) and the S0 -->S1 transition energy. As a result, a superior epsilon value was observed for D-IDT-A, whereas a bathochromic shift in the absorption occurred in A-IDT-D. The larger epsilon value of D-IDT-A together with its more favorable energy level relative to TiO2 led to a higher power conversion efficiency of 7.41 % for the D-IDT-A-based DSSC, retaining approximately 95 % of the N719-based DSSC efficiency. This work manifests the clear structure-property relationship for the case of donor and acceptor components being connected by an unsymmetrical pi linker and provides insights for molecular engineering of organic sensitizers. CI - (c) 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. FAU - Chou, Shu-Hua AU - Chou SH AD - Department of Chemistry, National Taiwan University, Taipei 10617 (Taiwan). FAU - Tsai, Chih-Hung AU - Tsai CH FAU - Wu, Chung-Chih AU - Wu CC FAU - Kumar, Dhirendra AU - Kumar D FAU - Wong, Ken-Tsung AU - Wong KT LA - eng PT - Journal Article DEP - 20141016 PL - Germany TA - Chemistry JT - Chemistry (Weinheim an der Bergstrasse, Germany) JID - 9513783 OTO - NOTNLM OT - donor-pi-acceptor-acceptor OT - dyes/pigments OT - indenothiophenes OT - intramolecular charge transfer OT - organic sensitizers OT - solar cells EDAT- 2014/10/18 06:00 MHDA- 2014/10/18 06:01 CRDT- 2014/10/18 06:00 PHST- 2014/05/19 00:00 [received] PHST- 2014/10/18 06:00 [entrez] PHST- 2014/10/18 06:00 [pubmed] PHST- 2014/10/18 06:01 [medline] AID - 10.1002/chem.201403584 [doi] PST - ppublish SO - Chemistry. 2014 Dec 8;20(50):16574-82. doi: 10.1002/chem.201403584. Epub 2014 Oct 16.