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Triptycene

CAS No.:
477-75-8
Catalog Number:
AG0039C0
Molecular Formula:
C20H14
Molecular Weight:
254.3252
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1g
98%
In Stock USA
United States
$25
- +
5g
98%
In Stock USA
United States
$75
- +
10g
98%
In Stock USA
United States
$137
- +
25g
98%
In Stock USA
United States
$300
- +
100g
98%
In Stock USA
United States
$900
- +
Product Description
Catalog Number:
AG0039C0
Chemical Name:
Triptycene
CAS Number:
477-75-8
Molecular Formula:
C20H14
Molecular Weight:
254.3252
MDL Number:
MFCD00003813
IUPAC Name:
pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
InChI:
InChI=1S/C20H14/c1-2-8-14-13(7-1)19-15-9-3-5-11-17(15)20(14)18-12-6-4-10-16(18)19/h1-12,19-20H
InChI Key:
NGDCLPXRKSWRPY-UHFFFAOYSA-N
SMILES:
c1ccc2c(c1)C1c3c(C2c2c1cccc2)cccc3
EC Number:
207-519-3
UNII:
CL32869MEP
NSC Number:
122926
Properties
Complexity:
279  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
254.11g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
0
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
254.332g/mol
Monoisotopic Mass:
254.11g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
0A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.8  
Literature
Title Journal
Triptycene based luminescent metal-organic gels for chemosensing. Chemical communications (Cambridge, England) 20121121
Synthesis, structures, and solid state self-assemblies of formyl and acetyl substituted triptycenes and their derivatives. The Journal of organic chemistry 20121019
Isomeric differentiation of polycyclic aromatic hydrocarbons using silver nitrate reactive desorption electrospray ionization mass spectrometry. Rapid communications in mass spectrometry : RCM 20120915
A C2-symmetric, basic Fe(III) carboxylate complex derived from a novel triptycene-based chelating carboxylate ligand. Dalton transactions (Cambridge, England : 2003) 20120821
A triptycene-based approach to solubilising carbon nanotubes and C60. Chemistry (Weinheim an der Bergstrasse, Germany) 20120709
A special conjugated model around sp3 carbon atoms: density functional theory study on the homoaromatic electron delocalization and applications of benzo-fused tetra(triptycene)porphyrins. Chemphyschem : a European journal of chemical physics and physical chemistry 20120604
Polycyclic aromatic triptycenes: oxygen substitution cyclization strategies. Journal of the American Chemical Society 20120502
Synthesis of polycyclic aromatic hydrocarbon-based nanovehicles equipped with triptycene wheels. Chemistry (Weinheim an der Bergstrasse, Germany) 20120305
Synthesis of triptycene-derived macrotricyclic host containing two dibenzo-[18]-crown-6 moieties and its complexation with paraquat derivatives: Li(+)-ion-controlled binding and release of the guests in the complexes. The Journal of organic chemistry 20120302
Building large supramolecular nanocapsules with europium cations. Chemical communications (Cambridge, England) 20120130
High CO2 uptake and selectivity by triptycene-derived benzimidazole-linked polymers. Chemical communications (Cambridge, England) 20120128
Triptycene diols: a strategy for synthesizing planar π systems through catalytic conversion of a poly(p-phenylene ethynylene) into a poly(p-phenylene vinylene). Angewandte Chemie (International ed. in English) 20120127
Molecular spur gears comprising triptycene rotators and bibenzimidazole-based stators. Journal of the American Chemical Society 20120125
Charge delocalization in self-assembled mixed-valence aromatic cation radicals. Langmuir : the ACS journal of surfaces and colloids 20120110
Formation of 1:2 host-guest complexes based on triptycene-derived macrotricycle and paraquat derivatives: anion-π interactions between PF6(-) and bipyridinium rings in the solid state. Organic letters 20111021
Design and synthesis of a novel triptycene-based ligand for modeling carboxylate-bridged diiron enzyme active sites. Organic letters 20111007
1-Iodo-triptycene. Acta crystallographica. Section E, Structure reports online 20110901
Two-step synthesis of hexaammonium triptycene: an air-stable building block for condensation reactions to extended triptycene derivatives. The Journal of organic chemistry 20110805
Novel triptycene-derived hosts: synthesis and their applications in supramolecular chemistry. Chemical communications (Cambridge, England) 20110214
Triptycene: no homoconjugation effect for extending optical properties of π-conjugated oligomers. Organic letters 20101119
Isolation of rotational isomers and developments derived therefrom. Proceedings of the Japan Academy. Series B, Physical and biological sciences 20101111
Oxadisilole fused triptycene and extended triptycene: precursors of triptycyne and extended triptycyne. The Journal of organic chemistry 20101105
Quantification of CH···π interactions: implications on how substituent effects influence aromatic interactions. Chemistry (Weinheim an der Bergstrasse, Germany) 20101102
Isomeric squaraine-based [2]pseudorotaxanes and [2]rotaxanes: synthesis, optical properties, and their tubular structures in the solid state. Chemistry (Weinheim an der Bergstrasse, Germany) 20100726
Triptycene-derived calix[6]arenes: synthesis, structures, and their complexation with fullerenes C60 and C70. Chemistry (Weinheim an der Bergstrasse, Germany) 20100719
Lewis-base adducts of 9,10-dihydro-9,10-diboraanthracene: ditopic hydroboration reagents and a B-N analogue of triptycene. Chemical communications (Cambridge, England) 20100528
Synthesis and structure of D(3h)-symmetric triptycene trimaleimide. Molecules (Basel, Switzerland) 20100107
Iptycenes in supramolecular and materials chemistry. Chemical Society reviews 20091201
Triptycene-derived N(H)-bridged azacalixarenes: synthesis, structure, and encapsulation of small neutral molecules in the solid state. Organic letters 20091119
A triphenylene-based triptycene with large free volume synthesized by zirconium-mediated biphenylation. The Journal of organic chemistry 20090102
A molecular paddlewheel with a sliding organometallic latch: syntheses, X-ray crystal structures and dynamic behaviour of [Cr(CO)3{eta(6)-2-(9-triptycyl)indene}], and of [M(CO)3{eta(5)-2-(9-triptycyl)indenyl}] (M = Mn, Re). Chemistry (Weinheim an der Bergstrasse, Germany) 20090101
77Se NMR chemical shifts of 9-(arylselanyl)triptycenes: new standard for planar structures of ArSeR and applications to determine the structures in solutions. The Journal of organic chemistry 20081205
Guest-dependent complexation of triptycene-based macrotricyclic host with paraquat derivatives and secondary ammonium salts: a chemically controlled complexation process. The Journal of organic chemistry 20080905
Iptycenes in the design of high performance polymers. Accounts of chemical research 20080901
Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold. Chemical communications (Cambridge, England) 20080407
Quantitative study of interactions between oxygen lone pair and aromatic rings: substituent effect and the importance of closeness of contact. The Journal of organic chemistry 20080118
Synthesis and structure of a triptycene-based nanosized molecular cage. The Journal of organic chemistry 20071123
Synthesis and structural investigation of new triptycene-based ligands: en route to shape-persistent dendrimers and macrocycles with large free volume. The Journal of organic chemistry 20071109
Triptycenediols by rhodium-catalyzed [2+2+2] cycloaddition. Organic letters 20070830
Excited-state dynamics of donor-acceptor bridged systems containing a boron-dipyrromethene chromophore: interplay between charge separation and reorientational motion. The journal of physical chemistry. A 20070628
Joining the rings: the preparation of 2- and 3-indenyl-triptycenes, and curious related processes. Organic & biomolecular chemistry 20070621
Triptycene-based expanded oxacalixarenes: synthesis, structure, and tubular assemblies in the solid state. The Journal of organic chemistry 20070511
The potential of organic polymer-based hydrogen storage materials. Physical chemistry chemical physics : PCCP 20070421
Enthalpy (DeltaH) and entropy (DeltaS) for pi-stacking interactions in near-sandwich configurations: relative importance of electrostatic, dispersive, and charge-transfer effects. The Journal of organic chemistry 20070330
Progress toward a rationally designed, chemically powered rotary molecular motor. Journal of the American Chemical Society 20070117
Antitumor triptycene analogs directly interact with isolated mitochondria to rapidly trigger markers of permeability transition. Anticancer research 20070101
Spontaneous formation of triptycene supramolecules on surfaces. The journal of physical chemistry. B 20061019
Robust non-interpenetrating coordination frameworks from new shape-persistent building blocks. Inorganic chemistry 20060220
Antitumor triptycene analogs induce a rapid collapse of mitochondrial transmembrane potential in HL-60 cells and isolated mitochondria. International journal of oncology 20060101
Antitumor triptycene bisquinones induce a caspase-independent release of mitochondrial cytochrome c and a caspase-2-mediated activation of initiator caspase-8 and -9 in HL-60 cells by a mechanism which does not involve Fas signaling. Anti-cancer drugs 20041101
Kinetic stabilization of the o-quinoidal 3,4-benzotropone system. Organic & biomolecular chemistry 20040907
Molecular design of free volume as a route to low-kappa dielectric materials. Journal of the American Chemical Society 20031119
Kinetic stabilization of primary hydrides of main group elements. The synthesis of an air-stable, crystalline arsine and silane. Inorganic chemistry 20031020
Antitumor triptycene bisquinones: a novel synthetic class of dual inhibitors of DNA topoisomerase I and II activities. Anti-cancer drugs 20030801
Synthesis and activity on free radical processes and inflammation of 9,10-dihydro-5,8-dimethoxy-triptycene-quinones. European journal of medicinal chemistry 20030601
Induction of poly(ADP-ribose) polymerase-1 cleavage by antitumor triptycene bisquinones in wild-type and daunorubicin-resistant HL-60 cell lines. Cancer letters 20021215
Solid-state molecular folding and supramolecular structures of triptycene-derived secondary dicarboxamides. The Journal of organic chemistry 20021018
Conjugated polymer liquid crystal solutions: control of conformation and alignment. Journal of the American Chemical Society 20020821
Octaphenylbiphenylene and dodecaphenyltriptycene. Journal of the American Chemical Society 20020710
Among substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetraones, the lead antitumor triptycene bisquinone TT24 blocks nucleoside transport, induces apoptotic DNA fragmentation and decreases the viability of L1210 leukemic cells in the nanomolar range of daunorubicin in vitro. Anti-cancer drugs 20020701
Triptycene quinones in synthesis: preparation of triptycene cyclopentenedione and its reactivity as a dienophile. The Journal of organic chemistry 20020628
Using 'internal free volume' to increase chromophore alignment. Journal of the American Chemical Society 20020417
A synthetic triptycene bisquinone, which blocks nucleoside transport and induces DNA fragmentation, retains its cytotoxic efficacy in daunorubicin-resistant HL-60 cell lines. International journal of oncology 20011201
The cytosolic receptor binding affinities and AHH induction potencies of 29 polynuclear aromatic hydrocarbons. Toxicology letters 19861101
Properties