DOI: 10.1002/anie.201204604. Elastic and Bendable Caffeine Cocrystals: Implications for the Design of Flexible Organic Materials

Elastic and Bendable Caffeine Cocrystals: Implications for the Design of Flexible Organic Materials

10.1002/anie.201204604

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Ghosh, S., & Reddy, C. M. (2012). Elastic and Bendable Caffeine Cocrystals: Implications for the Design of Flexible Organic Materials. Angewandte Chemie International Edition, 51(41), 10319â10323. Portico.

Authors 2

Soumyajit Ghosh (first)
C. Malla Reddy (additional)

References 59 Referenced 414

10.1002/ange.201107167
10.1002/anie.201107167
10.1039/C1JM14721H
10.1021/cm102419z
10.1038/nmat2137
10.1038/nature08603
10.1002/ange.200702443
10.1002/anie.200702443
10.1038/nature09024
{'key': 'e_1_2_2_9_2', 'first-page': '512', 'volume': '3', 'author': 'Cao Y.', 'year': '2008', 'journal-title': 'Nat. Mater.'} / Nat. Mater. by Cao Y. (2008)
10.1039/c2ce25100k
10.1039/c1sc00430a
10.1002/adma.200900533
10.1021/cg0607710
10.1002/ange.201104164
10.1002/anie.201104164
10.1002/adfm.201000902
10.1126/science.293.5532.1119
10.1021/ja110619k
10.1038/nmat2704
10.1039/b600098n
10.1038/47083
10.1038/25322
10.1126/science.276.5315.1112
10.1083/jcb.200601060
10.1002/chem.200500983
10.1039/c003466e
10.1039/c2ce06754d
10.1039/b505103g
10.1021/cg060398w
10.1002/ange.201105585
10.1002/anie.201105585
10.1021/ja100844m
{'key': 'e_1_2_2_38_2', 'volume-title': 'Crystal Engineering: The Design of Organic Solids', 'author': 'Desiraju G. R.', 'year': '1989'} / Crystal Engineering: The Design of Organic Solids by Desiraju G. R. (1989)
10.1002/ange.200700534
10.1002/anie.200700534
{'key': 'e_1_2_2_40_2', 'volume-title': 'Frontiers in Crystal Engineering', 'year': '2006'} / Frontiers in Crystal Engineering (2006)
Smaller crystallization batches yielded two other new unsolvated cocrystal polymorphs but they did not show elastic nature.
10.1021/ja302991b
Crystal data for1: orthorhombic Fdd2 a=32.784(9) b=55.541(15) c=3.9564(12) Å α=β=γ=90° V=7191(4) Å3 ρcalcd=1.566 g cm−3 Z=16 F(000)=3488 μ=0.266 mm−1 MoKαradiation (μ=0.71070 Å) T=100(2) 5007 collected reflections 1700 unique reflections (R(int)=0.038) 1531 observed reflections [I>2σ(I)] θmax=20.76° R1(obs)=0.038 wR1(obs)=0.0888 R2(all)=0.0451 wR2(all)=0.0932. CCDC 885350 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
Cambridge Structural Database (CSD version 5.33 2012) search revealed such disorder in all theortho‐Cl substituted nitrobenzenes.
{'key': 'e_1_2_2_45_2', 'volume-title': 'Mechanical Metallurgy', 'author': 'Bacon) G. E. Dieter (adapted by D.', 'year': '1988'} / Mechanical Metallurgy by Bacon) G. E. Dieter (adapted by D. (1988)
10.1103/PhysRevLett.76.2511
10.1021/jp991513z
{'key': 'e_1_2_2_49_2', 'volume-title': 'An Introduction to the Properties of Condensed Matter', 'author': 'Barber D. J.', 'year': '1989'} / An Introduction to the Properties of Condensed Matter by Barber D. J. (1989)
{'key': 'e_1_2_2_50_2', 'first-page': '637', 'volume-title': 'Atkin’s Physical Chemistry', 'author': 'Atkins P.', 'year': '2006'} / Atkin’s Physical Chemistry by Atkins P. (2006)
10.1021/nl050469y
10.1002/ange.201106652
10.1002/anie.201106652

Dates

Type	When
Created	12 years, 11 months ago (Sept. 11, 2012, 10:07 p.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 8:18 a.m.)
Indexed	2 days, 6 hours ago (Aug. 21, 2025, 1:54 p.m.)
Issued	12 years, 11 months ago (Sept. 11, 2012)
Published	12 years, 11 months ago (Sept. 11, 2012)
Published Online	12 years, 11 months ago (Sept. 11, 2012)
Published Print	12 years, 10 months ago (Oct. 8, 2012)

Funders 0

None

BibTeX

@article{Ghosh_2012, title={Elastic and Bendable Caffeine Cocrystals: Implications for the Design of Flexible Organic Materials}, volume={51}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.201204604}, DOI={10.1002/anie.201204604}, number={41}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Ghosh, Soumyajit and Reddy, C. Malla}, year={2012}, month=sep, pages={10319–10323} }

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