6.9 Experimental Section
189
Fig. 6.28 Excitation spectra of the crystalline sample 1 monitored at a 543 nm and b 498 nm. The
excitation spectra were measured in variable temperatures, 298 K (gray bold line) and 195 K (black
bold line)
References
1. (a) Yan D, Evans DG (2014) Molecular crystalline materials with tunable luminescent properties: from polymorphs to multi-component solids. Mater Horiz 1:46–57. (b) Friend RH,
Gymer RW, Holmes AB, Burroughes JH, Marks RN (1999) Electroluminescence in conjugated polymers. Nature 397:121–128. (c) Mutai T, Satou H, Araki K (2005) Reproducible
on–off switching of solid-state luminescence by controlling molecular packing through heatmode interconversion. Nat Mater 4:685–687. (d) Sagara Y, Yamane S, Mitani M, Weder C,
Kato T (2016) Mechanoresponsive luminescent molecular assemblies: an emerging class of
materials. Adv Mater 28:1073–1095
2. Hong Y, Lam JWY, Tang BZ (2011) Aggregation-induced emission. Chem Soc Rev 40:5361–
5388
3. (a) Shustova NB, McCarthy BD, Dinc˘ a M (2011) Turn-on fluorescence in tetraphenylethylenebased metal–organic frameworks: an alternative to aggregation-induced emission. J Am Chem
Soc 133:20126–20129. (b) Shustova NB, Ong T-C, Cozzolino AF, Michalis VK, Griffin
RG, Dinc˘ a M (2012) Phenyl ring dynamics in a tetraphenylethylene-bridged metal–organic
framework: implications for the mechanism of aggregation-induced emission. J Am Chem
Soc 134:15061. (c) Hughs M, Jimenez M, Khan SI, Garcia-Garibay MA (2013) Synthesis,
rotational dynamics, and photophysical characterization of a crystalline linearly conjugated
phenyleneethynylene molecular dirotor. J Org Chem 78:5293–5302
4. (a) Vogelsberg CS, Garcia-Garibay MA (2012) Crystalline molecular machines: function,
phase order, dimensionality, and composition. Chem Soc Rev 41:1892–1910. (b) Khuong
TAV, Nuñez JE, Godinez CE, Garcia-Garibay MA (2006) Crystalline molecular machines: a
quest toward solid-state dynamics and function. Acc Chem Res 39:413–422. (c) Horansky RD,
Clarke LI, Winston EB, Price JC, Karlen SD, Jarowski PD, Santillan R, Garcia-Garibay MA
(2006) Dipolar rotor-rotor interactions in a difluorobenzene molecular rotor crystal. Phys Rev B
74:054306. (d) Shima T, Hampel F, Gladysz JA (2004) Molecular gyroscopes: {Fe(CO) 3 } and
{Fe(CO) 2 (NO)} + rotators encased in three-spoke stators; facile assembly by alkene metatheses. Angew Chem Int Ed 43:5537–5540. (e) Lang GM, Shima T, Wang L, Cluff KJ, Skopek
K, Hampel F, Blümel J, Gladysz JA (2016) Gyroscope-like complexes based on dibridgehead
diphosphine cages that are accessed by three-fold intramolecular ring closing metatheses and
encase Fe(CO) 3 , Fe(CO) 2 (NO) + , and Fe(CO) 3 (H) + rotators. J Am Chem Soc 138:7649–7663.
(f) Setaka W, Yamaguchi K (2012) A molecular balloon: expansion of a molecular gyrotop
cage due to rotation of the phenylene rotor. J Am Chem Soc 134:12458–12461. (g) Setaka
W, Yamaguchi K (2013) Order–disorder transition of dipolar rotor in a crystalline molecular
gyrotop and its optical change. J Am Chem Soc 135:14560–14563. (h) Akutagawa T, Koshinaka H, Sato D, Takeda S, Noro S-I, Takahashi H, Kumai R, Tokura Y, Nakamura T (2009)
189
Fig. 6.28 Excitation spectra of the crystalline sample 1 monitored at a 543 nm and b 498 nm. The
excitation spectra were measured in variable temperatures, 298 K (gray bold line) and 195 K (black
bold line)
References
1. (a) Yan D, Evans DG (2014) Molecular crystalline materials with tunable luminescent properties: from polymorphs to multi-component solids. Mater Horiz 1:46–57. (b) Friend RH,
Gymer RW, Holmes AB, Burroughes JH, Marks RN (1999) Electroluminescence in conjugated polymers. Nature 397:121–128. (c) Mutai T, Satou H, Araki K (2005) Reproducible
on–off switching of solid-state luminescence by controlling molecular packing through heatmode interconversion. Nat Mater 4:685–687. (d) Sagara Y, Yamane S, Mitani M, Weder C,
Kato T (2016) Mechanoresponsive luminescent molecular assemblies: an emerging class of
materials. Adv Mater 28:1073–1095
2. Hong Y, Lam JWY, Tang BZ (2011) Aggregation-induced emission. Chem Soc Rev 40:5361–
5388
3. (a) Shustova NB, McCarthy BD, Dinc˘ a M (2011) Turn-on fluorescence in tetraphenylethylenebased metal–organic frameworks: an alternative to aggregation-induced emission. J Am Chem
Soc 133:20126–20129. (b) Shustova NB, Ong T-C, Cozzolino AF, Michalis VK, Griffin
RG, Dinc˘ a M (2012) Phenyl ring dynamics in a tetraphenylethylene-bridged metal–organic
framework: implications for the mechanism of aggregation-induced emission. J Am Chem
Soc 134:15061. (c) Hughs M, Jimenez M, Khan SI, Garcia-Garibay MA (2013) Synthesis,
rotational dynamics, and photophysical characterization of a crystalline linearly conjugated
phenyleneethynylene molecular dirotor. J Org Chem 78:5293–5302
4. (a) Vogelsberg CS, Garcia-Garibay MA (2012) Crystalline molecular machines: function,
phase order, dimensionality, and composition. Chem Soc Rev 41:1892–1910. (b) Khuong
TAV, Nuñez JE, Godinez CE, Garcia-Garibay MA (2006) Crystalline molecular machines: a
quest toward solid-state dynamics and function. Acc Chem Res 39:413–422. (c) Horansky RD,
Clarke LI, Winston EB, Price JC, Karlen SD, Jarowski PD, Santillan R, Garcia-Garibay MA
(2006) Dipolar rotor-rotor interactions in a difluorobenzene molecular rotor crystal. Phys Rev B
74:054306. (d) Shima T, Hampel F, Gladysz JA (2004) Molecular gyroscopes: {Fe(CO) 3 } and
{Fe(CO) 2 (NO)} + rotators encased in three-spoke stators; facile assembly by alkene metatheses. Angew Chem Int Ed 43:5537–5540. (e) Lang GM, Shima T, Wang L, Cluff KJ, Skopek
K, Hampel F, Blümel J, Gladysz JA (2016) Gyroscope-like complexes based on dibridgehead
diphosphine cages that are accessed by three-fold intramolecular ring closing metatheses and
encase Fe(CO) 3 , Fe(CO) 2 (NO) + , and Fe(CO) 3 (H) + rotators. J Am Chem Soc 138:7649–7663.
(f) Setaka W, Yamaguchi K (2012) A molecular balloon: expansion of a molecular gyrotop
cage due to rotation of the phenylene rotor. J Am Chem Soc 134:12458–12461. (g) Setaka
W, Yamaguchi K (2013) Order–disorder transition of dipolar rotor in a crystalline molecular
gyrotop and its optical change. J Am Chem Soc 135:14560–14563. (h) Akutagawa T, Koshinaka H, Sato D, Takeda S, Noro S-I, Takahashi H, Kumai R, Tokura Y, Nakamura T (2009)