Anomalous crystal packing of iptycene secondary diamides leading to novel chain and channel networks

Yang, Jye‐Shane; Liu, Chia-Peng; Lee, Gene‐Hsiang

doi:10.1016/s0040-4039(00)01379-4

Cited by 24 publications

(21 citation statements)

References 22 publications

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“…3 Crystal packing diagrams of 57 showing (a) the extended conformation and the stacking of N-acetylsulfanilyl substituents; (b) pentiptycene pillars; (c) the top view of zigzag pentiptycene walls and channels (methanol solvent molecules included), and (d) the effective sizes of channels by a space-filling model. Adapted from Tetrahedron Lett., 2000, 41, 7911 39.…”

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confidence: 99%

Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

2008

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The progress of pentiptycene chemistry is reviewed. Pentiptycene belongs to the iptycene family and possesses a rigid, aromatic, and H-shaped scaffold. An important feature for pentiptycene vs. triptycene is the presence of a 'sterically shielded' central benzene ring. Such a feature has led to the use of pentiptycene as a conformational regulator and in the formation of functional molecules, including fluorescent chemosensors, molecular machines, low dielectric constant materials, and porous solids. The synthesis of these materials relies on central-ring prefunctionalized pentiptycene building blocks. A useful approach toward the preparation of these building blocks is the derivatization of pentiptycene quinone.

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confidence: 99%

Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

2008

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“…shielding a reactive center, 27,28 or creating a void space in condensed phases. 29,30 Specific fields include nanoporous organic frameworks, 31,32 light and/or redox-responsive molecular devices, [33][34][35][36] fluorescent chemosensors, [37][38][39][40][41][42] molecular hosts, 43,44 ligands, [45][46][47][48][49][50] polymer electrolyte membranes, 51,52 and light-emitting π-conjugated oligomers and polymers. [53][54][55][56] We report herein the structural impacts of iptycene scaffolds on the LE-ICT fluorescence behavior of DMABN through the investigation of the triptycene and pentiptycene derivatives DMACT and DMACP.…”

Section: Introductionmentioning

confidence: 99%

Effects of iptycene scaffolds on the photoluminescence of N, N-dimethylaminobenzonitrile and its analogues

Tan

Chetti

Liu

et al. 2014

Photochem Photobiol Sci

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To understand the effect of iptycene scaffolds on the locally excited (LE) and intramolecular charge transfer (ICT) fluorescence of aminobenzonitriles, a series of triptycene and pentiptycene derivatives were synthesized and their molecular structures and photophysical properties were characterized and compared with the parent phenylene systems, 4-(N-methylamino)benzonitrile (MABN), 4-(N,N-dimethylamino)benzonitrile (DMABN), and 4-(N-phenylamino)benzonitrile (PABN). The iptycene effect does not change the nature of the fluorescing states for each amino donor system, i.e., the MA, PA, and DMA series display LE-only, ICT-only, and LE-ICT dual fluorescences, respectively. However, the iptycene scaffolds impose a significant modification of the absorption and emission spectra, fluorescence quantum efficiency and lifetimes, and the interplay of LE and ICT states. The observed iptycene effect has been discussed with three factors: (1) steric effect on increasing the amino twist angle, (2) steric shielding of solvation to the aminobenzonitrile core, and (3) hyperconjugation interactions of the aminobenzonitrile core with the peripheral phenylene groups of iptycene.

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“…2.2]octane central unit. [12][13][14][15][16] In cases where iptycene units are used in conjugated polymers, they show high stability and amplified fluorescent character playing a crucial role as a sensor for nitroaromatic explosives at gaseous phase. 17 Iptycenes are also utilized to produce low dielectric constant polymeric materials having improved thermal stability and high glass-transition temperatures (T g ).…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of heat-resistant polyimide/titanium dioxide nanocomposite films containing triptycene side units by sol–gel processes

Rafiee

Mallakpour

Hatamvand

2013

High Performance Polymers

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Thermally stable polyimide/titanium dioxide (PI/TiO 2 ) hybrid nanocomposite films have been successfully synthesized through the in situ formation of TiO 2 within a PI matrix via sol-gel process. Poly(amic acid) (PAA) solutions are prepared from bis(4-aminophenoxy)phenyl triptycene and 3,3 0 ,4,4 0 -benzophenone tetracarboxylic dianhydride in N-methyl-2pyrrolidinone solvent. The different amounts of tetraethyl orthotitanate and actylacetone (acac) are incorporated into PAA matrix, and then thermally imidized to form PI/TiO 2 . The chelating agent, acac, was applied to reduce the gelation rate of titanium alkoxide. Thermal decomposition temperatures with a 10% weight loss are in excess of 510 C, and char yields at 800 C under nitrogen atmosphere are higher than 69%. The chemical and morphological structures of the hybrid nanocomposites were characterized using Fourier transform infrared spectroscopy, x-ray diffraction, and transmission electron microscopy. The results show that the TiO 2 particles are well dispersed in the PI matrix with particle size between 10 and 30 nm in diameter.

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Anomalous crystal packing of iptycene secondary diamides leading to novel chain and channel networks

Cited by 24 publications

References 22 publications

Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold

Effects of iptycene scaffolds on the photoluminescence of N, N-dimethylaminobenzonitrile and its analogues

Preparation and characterization of heat-resistant polyimide/titanium dioxide nanocomposite films containing triptycene side units by sol–gel processes

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