Organic Letters
Letter
(5) Levine, P. M.; Carberry, T. P.; Holub, J. M.; Kirschenbaum, K. Med.
Chem. Commun. 2013, 4, 493−509.
(6) Fasting, C.; Schalley, C. A.; Weber, M.; Seitz, O.; Hecht, S.; Koksch,
B.; Dernedde, J.; Graf, C.; Knapp, E.-W.; Haag, R. Angew. Chem., Int. Ed.
2012, 51, 10472−10498.
(21) (a) Belaissaoui, A.; Cowling, S. J.; Saez, I. M.; Goodby, J. W. Soft
Matter 2010, 6, 1958−1963. (b) Belaissaoui, A.; Saez, I. M.; Cowling, S.
J.; Zeng, X.; Goodby, J. W. Chem.Eur. J. 2012, 18, 2366−2373.
(22) Baars, M. W. P. L.; Sontjens, S. H. M.; Fischer, H. M.; Peerlings,
̈
H. W. I.; Meijer, E. W. Chem.Eur. J. 1998, 4, 2456−2466.
(23) Hall, A. W.; Lacey, D.; Hill, J. S.; McDonnell, D. G. Supramol. Sci.
1994, 1, 21−32.
(24) Compound 4 did not fully dissolve at 0.1 M concentration in
THF, CH2Cl2, CHCl3, toluene, EtOAc, EtOH, or MeCN, even at the
boiling point of the solvent.
(25) (a) Koszelewski, D.; Szymanski, W.; Krysiak, J.; Ostaszewski, R.
Synth. Commun. 2008, 38, 1120−1127. (b) Bousquet, T.; Jida, M.;
Soueidan, M.; Deprez-Poulain, R.; Agbossou-Niedercorn, F.; Pelinski, L.
Tetrahedron Lett. 2012, 53, 306−308.
(26) (a) Jee, J.-A.; Spagnuolo, L. A.; Rudick, J. G. Org. Lett. 2012, 14,
3292−3295. (b) Baker, R. H.; Stanonis, D. J. Am. Chem. Soc. 1951, 73,
669−702.
(27) Kato, T.; Mizoshita, N.; Kishimoto, K. Angew. Chem., Int. Ed.
2006, 45, 38−68.
(7) (a) Saez, I. M.; Goodby, J. W. Struct. Bonding (Berlin) 2008, 128, 1−
62. (b) Lehmann, M. Top. Curr. Chem. 2012, 318, 193−224.
(8) Passerini, M. Gazz. Chim. Ital. 1921, 51, 126−129.
(9) An astute reviewer of this manuscript called to our attention that,
for mesogenic compounds, the term “star-branched” is reserved for
molecules with a symmetric core regardless of the symmetry of the
molecule (viz. ref 7b.). Mesogens with an α-acyloxyamide core formally
belong to the family of mesogens called tripedes: Saez, I. M.; Goodby, J.
W. J. Mater. Chem. 2005, 15, 26−40.
(10) (a) Fisch, M. R.; Kumar, S. Introduction to Liquid Crystals. In
Liquid Crystals: Experimental Study of Physical Properties and Phase
Transitions; Kumar, S., Ed.; Cambridge University Press: New York,
2001; pp 1−28. (b) Collings, P. J.; Hird, M. Introduction to Liquid
Crystals Chemistry and Physics; Taylor & Francis: New York, 1997.
(11) (a) Geelhaar, T.; Griesar, K.; Reckmann, B. Angew. Chem., Int. Ed.
2013, 52, 8798−8809. (b) Bremer, M.; Kirsch, P.; Klasen-Memmer, M.;
Tarumi, K. Angew. Chem., Int. Ed. 2013, 52, 8880−8896.
(12) (a) Mehl, G.; Thornton, A. J.; Goodby, J. W. Mol. Cryst. Liq. Cryst.
1999, 332, 455−461. (b) Zhang, B.-Y.; Yao, D.-S.; Meng, F.-B.; Li, Y.-H.
J. Mol. Struct. 2005, 741, 135−140.
(13) (a) Donnio, B.; Guillon, D. Adv. Polym. Sci. 2006, 201, 45−155.
(b) Donnio, B.; Buathong, S.; Bury, I.; Guillon, D. Chem. Soc. Rev. 2007,
36, 1495−1513. (c) Rosen, B. M.; Wilson, C. J.; Wilson, D. A.; Peterca,
M.; Imam, M. R.; Percec, V. Chem. Rev. 2009, 109, 6275−6540.
(d) Tschierske, C. Angew. Chem., Int. Ed. 2013, 52, 8828−8878.
(14) (a) Chen, S. H.; Mastrangelo, J. C.; Shi, H.; Bashir-Hashemi, A.;
(28) Passerini, M. Gazz. Chim. Ital. 1924, 54, 529−540.
(29) Extance, A. R.; Benzies, D. W. M.; Morrish, J. J. QSAR Comb. Sci.
2006, 25, 484−490.
(30) Fan, L.; Adams, A. M.; Polisar, J. G.; Ganem, B. J. Org. Chem. 2008,
73, 9720−9726.
(31) Ugi, I.; Steinbruckner, C. Chem. Ber./Recl. 1961, 94, 2802−2814.
̈
(32) See the Supporting Information for two additional examples of
AB2 compounds, S14 and S16.
(33) Neubert, M. E. Characterization of Mesophase Types and
Transitions. In Liquid Crystals: Experimental Study of Physical Properties
and Phase Transitions; Kumar, S., Ed.; Cambridge University Press: New
York, 2001; pp 29−64.
(34) (a) Chen, S. H.; Mastrangelo, J. C.; Blanton, T. N.; Bashir-
Hashemi, A.; Marshall, K. L. Liq. Cryst. 1996, 21, 683−694. (b) Kim, D.-
Y.; Park, M.; Lee, S.-A.; Kim, S.; Hsu, C.-H.; Kim, N.; Kuo, S.-W.; Yoon,
T.-H.; Jeong, K.-U. Soft Matter 2015, 11, 58−68.
Li, J.; Gelber, N. Macromolecules 1995, 28, 7775−7778. (b) Beltran
Serrano, J. L.; Sierra, T.; Gimenez, R. Org. Lett. 2010, 12, 1404−1407.
(c) Beltran, E.; Serrano, J. L.; Sierra, T.; Gimenez, R. J. Mater. Chem.
2012, 22, 7797−7805.
́
, E.;
́
́
́
(35) Siamaki, A. R.; Sakalauskas, M.; Arndtsen, B. A. Angew. Chem., Int.
Ed. 2011, 50, 6552−6556.
(15) (a) Ungar, G.; Tschierske, C.; Abetz, V.; Holyst, R.; Bates, M. A.;
Liu, F.; Prehm, M.; Kieffer, R.; Zeng, X.; Walker, M.; Glettner, B.;
Zywocinski, A. Adv. Funct. Mater. 2011, 21, 1296−1323. (b) Kim, Y. H.;
Yoon, D. K.; Jung, H.-T. J. Mater. Chem. 2009, 19, 9091−9102.
(36) Kreye, O.; Tot
1790−1792.
́
h, T.; Meier, M. A. R. J. Am. Chem. Soc. 2011, 133,
(c) Goodby, J. W.; Saez, I. M.; Cowling, S. J.; Gortz, V.; Draper, M.; Hall,
̈
A. W.; Sia, S.; Cosquer, G.; Lee, S.-E.; Raynes, E. P. Angew. Chem., Int. Ed.
2008, 47, 2754−2787. (d) Goodby, J. W.; Davis, E. J.; Mandle, R. J.;
Cowling, S. J. Isr. J. Chem. 2012, 52, 863−880. (e) Fleischmann, E.-K.;
Zentel, R. Angew. Chem., Int. Ed. 2013, 52, 8810−8827. (f) Laschat, S.;
Baro, A.; Steinke, N.; Giesselmann, F.; Hagele, C.; Scalia, G.; Judele, R.;
̈
Kapatsina, E.; Sauer, S.; Schreivogel, A.; Tosoni, M. Angew. Chem., Int.
Ed. 2007, 46, 4832−4887.
(16) (a) Goring, P.; Pelzl, G.; Diele, S.; Delavier, P.; Siemensmeyer, K.;
̈
Etzbach, K. H. Liq. Cryst. 1995, 19, 629−635. (b) Zab, K.; Joachimi, D.;
Agert, O.; Neumann, B.; Tschierske, C. Liq. Cryst. 1995, 18, 489−494.
(c) Lehmann, M.; Gearba, R. I.; Ivanova, D. A.; Koch, M. H. J. Mol. Cryst.
Liq. Cryst. 2004, 411, 397−406. (d) Tomczyk, J.; Sobolewska, A.; Nagy,
Z. T.; Guillon, D.; Donnio, B.; Stumpe, J. J. Mater. Chem. C 2013, 1,
924−932. (e) Zelcer, A.; Donnio, B.; Bourgogne, C.; Cukiernik, F. D.;
Guillon, D. Chem. Mater. 2007, 19, 1992−2006. (f) Nagy, Z. T.;
Heinrich, B.; Guillon, D.; Tomczyk, J.; Stumpe, J.; Donnio, B. J. Mater.
Chem. 2012, 22, 18614−18622.
(17) (a) Lehmann, M.; Jahr, M. Chem. Mater. 2008, 20, 5453−5456.
(b) Lehmann, M.; Jahr, M.; Gutmann, J. J. Mater. Chem. 2008, 18,
2995−3003. (c) Weber, C. H. M.; Liu, F.; Zeng, X.-b.; Ungar, G.; Mullin,
N.; Hobbs, J. K.; Jahr, M.; Lehmann, M. Soft Matter 2010, 6, 5390−
5396.
(18) Saez, I. M.; Goodby, J. W. J. Mater. Chem. 2003, 13, 2727−2739.
(19) Lehmann, M.; Jahr, M. Org. Lett. 2006, 8, 721−723.
(20) (a) Lin, Y.-C.; Lai, C. K.; Chang, Y.-C.; Liu, K.-T. Liq. Cryst. 2002,
29, 237−242. (b) Chien, C.-W.; Liu, K.-T.; Lai, C. K. Liq. Cryst. 2004,
31, 1007−1017.
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