TY - JOUR
T1 - Impact of C-H···X (X = F, N) and π-π Interactions on Tuning the Degree of Charge Transfer in F6TNAP-Based Organic Binary Compound Single Crystals
AU - Hu, Peng
AU - Wang, Shancheng
AU - Chaturvedi, Apoorva
AU - Wei, Fengxia
AU - Zhu, Xiaoting
AU - Zhang, Xiaotao
AU - Li, Rongjin
AU - Li, Yongxin
AU - Jiang, Hui
AU - Long, Yi
AU - Kloc, Christian
N1 - This research is partially supported by grants from the National Research Foundation, Prime Minister’s Office, Singapore, under its Campus of Research Excellence and Technological Enterprise (CREATE) programme. The authors acknowledge financial support from the National Key R&D program (2017YFA0204503) and the National Natural Science Foundation of China (51733004).
Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/3/7
Y1 - 2018/3/7
N2 - Single crystals of four new charge transfer compounds, triphenylene (TP)-1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6TNAP), pyrene-F6TNAP, phenanthrene (PA)-F6TNAP, and naphtho[1,2-b:5,6-b']dithiophene (NDT)-F6TNAP, with needle-like morphologies and dark color were grown by chemical vapor transport. The influence of C-H···X (X = F, N) interactions as well π-π interactions on the degree of charge transfer (DCT) in these compounds was investigated. The results indicate that the DCT is proportional to the interplanar D-A distance along the π-π interaction direction in TP-F6TNAP, pyrene-F6TNAP, and PA-F6TNAP single crystals. With the decreasing of the D-A interplanar distance from 3.3560 Å of TP-F6TNAP to 3.3254 Å of PA-F6TNAP, the DCT is significantly increased from 0.03 ± 0.02 of TP-F6TNAP to 0.26 ± 0.03 of PA-F6TNAP, showing the strong relationship between π-π interactions and the DCT. In addition to π-π interactions, a stronger C-H···F interaction (C-H···F bond length: 2.3689 Å) is observed in NDT-F6TNAP, which exhibits larger contributions to the DCT of NDT-F6TNAP (0.46 ± 0.04). These results suggest that it is important to evaluate the DCT by considering the combination of π-π interactions and C-H···X (X = F, N) interactions in organic charge transfer compounds.
AB - Single crystals of four new charge transfer compounds, triphenylene (TP)-1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6TNAP), pyrene-F6TNAP, phenanthrene (PA)-F6TNAP, and naphtho[1,2-b:5,6-b']dithiophene (NDT)-F6TNAP, with needle-like morphologies and dark color were grown by chemical vapor transport. The influence of C-H···X (X = F, N) interactions as well π-π interactions on the degree of charge transfer (DCT) in these compounds was investigated. The results indicate that the DCT is proportional to the interplanar D-A distance along the π-π interaction direction in TP-F6TNAP, pyrene-F6TNAP, and PA-F6TNAP single crystals. With the decreasing of the D-A interplanar distance from 3.3560 Å of TP-F6TNAP to 3.3254 Å of PA-F6TNAP, the DCT is significantly increased from 0.03 ± 0.02 of TP-F6TNAP to 0.26 ± 0.03 of PA-F6TNAP, showing the strong relationship between π-π interactions and the DCT. In addition to π-π interactions, a stronger C-H···F interaction (C-H···F bond length: 2.3689 Å) is observed in NDT-F6TNAP, which exhibits larger contributions to the DCT of NDT-F6TNAP (0.46 ± 0.04). These results suggest that it is important to evaluate the DCT by considering the combination of π-π interactions and C-H···X (X = F, N) interactions in organic charge transfer compounds.
UR - http://www.scopus.com/inward/record.url?scp=85043350921&partnerID=8YFLogxK
U2 - 10.1021/acs.cgd.7b01669
DO - 10.1021/acs.cgd.7b01669
M3 - Journal article
AN - SCOPUS:85043350921
SN - 1528-7483
VL - 18
SP - 1776
EP - 1785
JO - Crystal Growth and Design
JF - Crystal Growth and Design
IS - 3
ER -
