Supporting Information Crystal Growth, HOMO-LUMO Engineering ...

Supporting Information Crystal Growth, HOMO-LUMO Engineering and Charge Transfer Degree in Perylene-FxTCNQ (x=1, 2, 4) Organic Charge Transfer Binary Compounds Peng Hu, † Kezhao Du, † Fengxia Wei, † Hui Jiang,*,† and Christian Kloc*,†

† School of Materials Science and Engineering, Nanyang Technological University, 639798 Singapore

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Figure S1. Solid state UV-Vis spectrum of perylene (solid black line), F1TCNQ (dash red line), F2TCNQ (dash blue line), F4TCNQ (dash green line), perylene-F1TCNQ (solid red line, perylene-F2TCNQ (solid blue line) and perylene-F4TCNQ (solid green line).

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Figure S2. The disordered Perylene-F1TCNQ, viewed along a direction. On this figure F atoms are drawing on two positions, randomly distributed with 73.6% at position 1 and 26.4% at position 2. These 2 sites are differentiated due to the monoclinic symmetry.

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Figure S3. Whole molecule disorder in perylene-F2TCNQ. The semi-transparent perylene and F2TCNQ molecules indicate the second set of orientations, viewed along c axis.

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Figure S4. C-H … N hydrogen bond interactions in perylene-FxTCNQ single crystals. (a) perylene-F1TCNQ; (b) perylene-F2TCNQ; (c) perylene-F4TCNQ.

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Figure S5. Halogen…halogen interactions in perylene-FxTCNQ single crystals. (a) peryleneF1TCNQ; (b) perylene-F2TCNQ; (c) perylene-F4TCNQ. S6

Table S1 Length of C-H…N hydrogen bond in perylene-FxTCNQ single crystals.

Perylene-F1TCNQ

Perylene-F2TCNQ Perylene-F4TCNQ

Crystals

Length (Å)

C8-H8…N1

2.5795

C13-H13…N2

2.7765

C14-H14…N1

2.6784

C2-H2…N3

2.4489

C8-N8…N3

2.5618

C5-H5…N2

3.2468

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