An early version of the data on PCBM adducts (just Bis I think at this stage?). This was put together very quickly, for a talk over in Chemistry.
The results that followed from this were the key ones of my PhD.
To form the SMILES strings for PCBM with arbitrary attachment points, I borrowed a PhD friend's indoor Football (which is the same shape) and used post-it notes to locate the sidechains, while I rotated in in front of my eyes + checked that it agreed with the hand-annotated Schlegel diagrams in my lab book that I had built for each adduct.
I had evidently already started a combinatory sift, and found the CPDT fullerene, though hadn't yet managed to calculate Tris adducts.
Jarvist Frost, James Kirkpatrick, Jenny Nelson
Physics Department, Imperial College London
SMILES (Simplified molecular input line entry specification)
HOMO: Highest Occupied KS
Energy Level (well defined)
HOMO+1: First virt KS orbital
(badly defined, but free)
SCF calculation of charged
molecule without nuclear
HOMO LUMO (eV)
C1: -5.22893 -3.46713
C2: -5.30618 -3.34498
C3: -5.30590 -3.4574
E': -5.28632 -3.34532
T1: -5.27054 -3.44314
T2: -5.29720 -3.4211
T3: -5.37526 -3.47596
T4: -5.32576 -3.43576
Lifted HOMO (effect on working cell?)
Lifted LUMO (~300meV c.f. Mono-pcbm)
Homo spin density on Thiophene unit
Thiophene unit fairly compact (effect on packing)
Further Work: Different adducts, higher order adducts
Understanding effect of varying Lumo of isomers on performance (fill factor?)
Combine with simplistic MD to generate amorphous films + charge transport studies
Comparison of DFT Methods for Molecular Orbital Eigenvalue Calculations –
Gang Zhang et al. J. Phys. Chem. A 2007, 111, 1554-1561
Principles of Fullerene Reactivity – Andreas Hirsch. Topics in Current Chemistry, Vol.
Fullerene Chemistry in Three Dimensions – Andreas Hirsch et al. Angew. Chem. Int.
Ed. Engl. 1994, 33, No. 4
The Addition Patterns of C60 Trisadducts – Francis Djojo et al. Eur. J. Org. Chem.
Lecture Notes on Fullerene Chemistry – Roger Taylor, Imperial College Press 1999
Pi-Conjugated Fullerene Adducts – Floris Berend Kooistra, PhD Thesis 2007,
University of Groningen
Acknowledgments and References
Jenny Nelson (Supervisor)
James Kirkpatrick (Gaussian Assistance + awk scripts)
Kevin Gilbert, Rajarshi Guha - Indiana University (smi23d coordinate generation)
Other Software: Openbabel, Gaussian 03, PyMol
High Performance Computing facility, Imperial College London (2.5 CPU-Years)