Tuning the structural and spectroscopic properties of donor-acceptor-donor oligomers via mutual X-bonding, H-bonding, and π-π interactionsElectronic supplementary information (ESI) available: Crystallographic data, details of the thermal analysis, details of the theoretical calculations, 1H NMR spectra, and supplementary results. CCDC 1813579 and 1813580. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8tc00074c
Presented are design strategies towards hierarchically assembling a C 2 -symmetric π-conjugated oligomer ( DAD-XB-Boc ) based on a donor-acceptor-donor motif through hydrogen bonding (HB), halogen bonding (XB), and π-stacking interactions. Upon co-crystallization with tetrafluoro-1,4-diiodobenzene (...
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Main Authors | , , , , , , , , |
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Format | Journal Article |
Published |
15.11.2018
|
Online Access | Get full text |
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Summary: | Presented are design strategies towards hierarchically assembling a
C
2
-symmetric π-conjugated oligomer (
DAD-XB-Boc
) based on a donor-acceptor-donor motif through hydrogen bonding (HB), halogen bonding (XB), and π-stacking interactions. Upon co-crystallization with tetrafluoro-1,4-diiodobenzene (
TFDIB
), single crystal X-ray analysis reveals highly directional XB induced 2D assemblies which further organize
via
π-π interactions. Crystal photoluminescence (PL) analysis indicates that the co-crystal exhibits a red shift in its PL spectrum with enhanced intensity compared to the mono-crystal. Pyrolytic cleavage and removal of the
t
-butyloxycarbonyl (Boc) groups of
DAD-XB-Boc
exposes complementary hydrogen bonding sites; the H-bonding capability of
DAD-XB-NH
is evident from thermal gravimetric analysis (TGA) and infrared (IR) spectroscopy. Overall, the data show that both halogen and hydrogen bonding can be used together with π-stacking interactions to enhance the solid-state properties of DAD oligomers essential for optoelectronic device applications. Ongoing work seeks to use such supramolecular approaches to control the nanoscale to microscale arrangement of molecules in thin films and increase device efficiency (
i.e.
, charge mobility).
Presented are design principles for the combinatory usage of HB, XB, and π-π interactions to enhance solid-state properties essential for optoelectronic device application. |
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Bibliography: | 1 For ESI and crystallographic data in CIF or other electronic format see DOI H NMR spectra, and supplementary results. CCDC 1813579 and 10.1039/c8tc00074c Electronic supplementary information (ESI) available: Crystallographic data, details of the thermal analysis, details of the theoretical calculations 1813580 |
ISSN: | 2050-7526 2050-7534 |
DOI: | 10.1039/c8tc00074c |