Chem, Volume 2

Supplemental Information

Materially Engineered Artificial Pollinators

Svetlana A. Chechetka, Yue Yu, Masayoshi Tange, and Eijiro Miyako

Supplemental Information

Table of contents

1. NMR and elemental analyses of synthesized ionic liquids

2. Optimal condition for gelation of ionic liquids

3. Chemical structures of various ionic liquids for synthesizing of ILGs

4. TGA measurements of ILGs

5. Cytotoxicity of ILG

6. Water tolerance and durability of ILG

7. Photochromic camouflage of ILG on flies

8. Artificial pollination by ILG-decollated hybrid ants

9. Spore collection by ILG-modified functional fibers

10. Fluorescent microscopic analyses of artificial pollinations

11. Spore collection by controlling of the artificial pollinator

Supplemental Figures & Table

1. NMR and elemental analyses of synthesized ionic liquids

Figure S1. 1H-NMR spectrum of [vbim][Cl] in DMSO-d6.

Figure S2. 1H-NMR spectrum of [vbim][PF6] in DMSO-d6.

Figure S3. Results of elemental analyses of [vbim][PF6] and [vbim][Cl].

2. Optimal condition for gelation of ionic liquids

Figure S4. Gelation of ionic liquids using different volumes of TEGDMA (left to right: 10, 20, 30, 50, and 100 μL).

Amount of BPO was 50 mg. Volumes of [vbim][PF6] and [bmim][PF6] were 100 and 100 μL, respectively.

Table S1. Phototriggered gelation using different concentrations of cross-linker and photoinitiator.

2H2MPP (µL)

TEGDMA

(µL)

1 5 10 50 100

1 G G G G Sol

5 G G G G G

10 G G G G G

50 PG PG G G G

100 Sol Sol PG G G

Abbreviations: G (Gel), PG (Partial gel), and Sol (Soluble).

Volumes of [vbim][PF6] and [bmim][PF6] were 100 and 100 μL, respectively.

3. Chemical structures of various ionic liquids for synthesizing of ILGs

Figure S5. Chemical structures of ionic liquids used for gelation. Abbreviations: 1-butyl-3-methylimidazolium

hexafluorophosphate ([bmim][PF6]), 1-hyxyl-3-methylimidazolium hexafluorophosphate ([hmim][PF6]),

1-octyl-3-methylimidazolium hexafluorophosphate ([omim][PF6]), 1-butyl-3-methylimidazolium

bis(trifluoromethylsulfonyl)imide ([bmim][Tf2N]), 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

([hmim][Tf2N]), and 1-octyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([omim][Tf2N]). All of the ionic

liquids are commercially available.

4. TGA measurements of ILGs

Figure S6. TGA curves of ILGs obtained for different volumes of cross-linker (A: 50 μL and B: 100 μL). Starting

weights of ILGs were (A) 5.2 and (B) 5.12 mg.

5. Cytotoxicity of ILG

Figure S7. Cell viability following treatment with ILG. Error bars represent standard deviations of five separate

measurements.

6. Water tolerance and durability of ILG

Figure S8. Water tolerance and durability of ILG. Error bars represent standard deviations of three separate

measurements.

7. Photochromic camouflage of ILG on flies

Figure S9. Photochromic camouflage of ILG-functionalized hybrid flies. Photographs of (A) UV- and (B) white

light-illuminated hybrid flies. (C) Photograph of a wild fly.

8. Artificial pollination by ILG-decollated hybrid ants

Figure S10. Experimental setup used for pollination of T. gesneriana flowers by ILG-functionalized hybrid ants.

Figure S11. SEM images of wild ant after incubation with T. gesneriana flowers overnight.

Figure S12. Number of pollen grains of T. gesneriana flowers per square cm on hybrid and wild ants. Error bars

represent standard deviations of three separate measurements.

9. Spore collection by ILG-modified functional fibers

Figure S13. SEM images of (A) nylon and (B) carbon fibers before and after coating with the ILGs. Volumes of

[vbim][PF6], [bmim][PF6], and TEGDMA were 100, 100, and 50 μL, respectively. Amount of BPO was 50 mg.

10. Fluorescent microscopic analyses of artificial pollinations

Figure S14. Fluorescent microscopy image of a flower pistil just after pollination by materially engineered artificial

pollinator.

Figure S15. Fluorescent microscopy images of pistils after pollination by materially engineered artificial pollinator

and overnight incubation: (A) UAV without ILG-coated vertically aligned animal hairs and (B) UAV with uncoated

vertically aligned animal hairs.

11. Spore collection by controlling of the artificial pollinator

Figure S16. Pollen collection efficiency of hybrid hairs by controlling of the artificial pollinator.

Figure S17. (A) Effect electrostatic irradiation time (10, 30, and 60 sec) on hair density. (B) Effect of hair density on

the collection of spores. Error bars represent standard deviations of three separate measurements.