Abstract
Scanning tunneling microscopy (STM) has become a staple surface microscopy technique for a number of research fields ranging from semiconductor research to heterogeneous catalysis. Pharmaceutical compounds, however, remain largely unstudied. Here we report the first STM study of carbamazepine (CBZ), an anti-epileptic drug, on Au(111) and Cu(111) surfaces. The analysis reveals that CBZ adopts unusual chiral molecular architectures on both metals. These previously unreported structures, which are strikingly different from CBZ packing arrangements observed in 3D crystal structures, indicate that the main molecular architecture is driven by a combination of CBZ intermolecular hydrogen bonding and metal-CBZ interactions. Comparison of the 2D molecular structures reveals large differences in local geometry and packing density that are dependent on the nature of the metal surface. These results have implications for the potential role of metal surfaces as heteronuclei or templating agents for controlling polymorph formation, which continues to be a problem for many compounds in the pharmaceutical industry including CBZ.
| Language | English |
|---|---|
| Pages | 5061-5068 |
| Number of pages | 8 |
| Journal | ACS Nano |
| Volume | 4 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - Sep 2010 |
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Keywords
- carbamazepine
- polymorph
- heteronuclei
- surface
- STM
- scanning-tunneling-microscopy
- Cambridge structural database
- self assembled monolayers
- crystal structures
- organic-molecules
- ultrahigh vacuum
- chirality
- organization
- network
Cite this
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Surface-mediated two-dimensional growth of the pharmaceutical carbamazepine. / Iski, Erin V.; Johnston, Blair F.; Florence, Alastair J.; Urquhart, Andrew J.; Sykes, E. Charles H.
In: ACS Nano, Vol. 4, No. 9, 09.2010, p. 5061-5068.Research output: Contribution to journal › Article
TY - JOUR
T1 - Surface-mediated two-dimensional growth of the pharmaceutical carbamazepine
AU - Iski, Erin V.
AU - Johnston, Blair F.
AU - Florence, Alastair J.
AU - Urquhart, Andrew J.
AU - Sykes, E. Charles H.
PY - 2010/9
Y1 - 2010/9
N2 - Scanning tunneling microscopy (STM) has become a staple surface microscopy technique for a number of research fields ranging from semiconductor research to heterogeneous catalysis. Pharmaceutical compounds, however, remain largely unstudied. Here we report the first STM study of carbamazepine (CBZ), an anti-epileptic drug, on Au(111) and Cu(111) surfaces. The analysis reveals that CBZ adopts unusual chiral molecular architectures on both metals. These previously unreported structures, which are strikingly different from CBZ packing arrangements observed in 3D crystal structures, indicate that the main molecular architecture is driven by a combination of CBZ intermolecular hydrogen bonding and metal-CBZ interactions. Comparison of the 2D molecular structures reveals large differences in local geometry and packing density that are dependent on the nature of the metal surface. These results have implications for the potential role of metal surfaces as heteronuclei or templating agents for controlling polymorph formation, which continues to be a problem for many compounds in the pharmaceutical industry including CBZ.
AB - Scanning tunneling microscopy (STM) has become a staple surface microscopy technique for a number of research fields ranging from semiconductor research to heterogeneous catalysis. Pharmaceutical compounds, however, remain largely unstudied. Here we report the first STM study of carbamazepine (CBZ), an anti-epileptic drug, on Au(111) and Cu(111) surfaces. The analysis reveals that CBZ adopts unusual chiral molecular architectures on both metals. These previously unreported structures, which are strikingly different from CBZ packing arrangements observed in 3D crystal structures, indicate that the main molecular architecture is driven by a combination of CBZ intermolecular hydrogen bonding and metal-CBZ interactions. Comparison of the 2D molecular structures reveals large differences in local geometry and packing density that are dependent on the nature of the metal surface. These results have implications for the potential role of metal surfaces as heteronuclei or templating agents for controlling polymorph formation, which continues to be a problem for many compounds in the pharmaceutical industry including CBZ.
KW - carbamazepine
KW - polymorph
KW - heteronuclei
KW - surface
KW - STM
KW - scanning-tunneling-microscopy
KW - Cambridge structural database
KW - self assembled monolayers
KW - crystal structures
KW - organic-molecules
KW - ultrahigh vacuum
KW - chirality
KW - organization
KW - network
U2 - 10.1021/nn100868r
DO - 10.1021/nn100868r
M3 - Article
VL - 4
SP - 5061
EP - 5068
JO - ACS Nano
T2 - ACS Nano
JF - ACS Nano
SN - 1936-0851
IS - 9
ER -