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P. W. Fowler School of Chemistry, University of Exeter, Stocker Road, Exeter, UK EX4 4QD Received 20th February 2002, Accepted 10th April 2002 First published as an Advance Article on the web 27th May 2002

Any Huckel p system with the Mobius-strip topology has a quotient property whereby its Huckel spectrum is the ungerade, and its adjacency spectrum the gerade half of the spectrum of a centrosymmetric cylindrical graph with twice as many vertices. Consequences include the spectral complementarity of Huckel and anti-Huckel monocycles, spectral embedding of twisted in untwisted cyclic polyacenes, and spectral inversion between inand out-of-plane p sub-systems of odd-numbered rings in cluster molecules. Cartesian coordinates for Mobius graphs can be derived from those of the cylindrical parent.

1. Introduction

Linked, knotted and twisted structures are increasingly common features of supramolecular chemistry and molecular biology.14 One of the simplest non-trivial topologies, the Mobius strip (or Mobius band) entered chemistry as a description for twisted polyenes5 and transition states of pericyclic reactions,6,7 but it is also encountered in molecular ground states, actual and predicted.813 In recreational mathematics much is made of the one-sidedness of this surface and its startling behaviour when cut along dierent closed curves.14 The point of departure of the present paper is a less well known topological property of the Mobius strip that has more direct chemical consequences. It is shown that the quotientdouble cover relationship between Mobius and cylindrical systems15 implies graph eigenvalue properties that in turn can explain the systematics of Huckel orbitals and energy levels in twisted p systems.

transported around the curve to return to its original position but with the anti-clockwise sense (Fig. 2); equivalently, a right-handed triple of unit vectors, two in the surface and one normal to it, can be converted into a left-handed system by transportation around the same curve.

In the usual intuitive construction, the Mobius band is ima gined as being formed by joining the ends of a long, thin, rectangular strip of paper with vanishing thickness, after making a half-twist so that what were originally diagonally opposite corners of the strip become identied (Fig. 1). This creates a surface M2 with just one face, as all points of the band can be reached from all others without crossing an edge, and that face is bounded by a single edge formed by the original long edges of the parent rectangular strip. As Klein16 observed, this curious one-sided surface is also non-orientable: there exist closed curves in M2 such that a circular arrow drawn with a clockwise sense around an origin in the surface can be

Fig. 1 Construction of the Mobius surface from a rectangle, by join ing two opposite edges with reversed sense (c ! a becoming b ! d).

Fig. 2 Non-orientability of the Mobius band: as a circular arrow is moved along the central line of the Mobius band, its sense changes from (a) clockwise to (e) anticlockwise.

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Phys. Chem. Chem. Phys., 2002, 4, 28782883 This journal is # The Owner Societies 2002

DOI: 10.1039/b201850k

Fig. 3 The ve surfaces obtained from the rectangle by edge identications: the cylinder C2, Mobius band M2, torus T2, Klein bottle K2 and projective plane P2. Shaded diagrams denote non-orientable surfaces.

In fact, the rectangular strip used for the construction of M2 can be used to produce no fewer than ve topological manifolds, three with the property of non-orientability. As shown schematically in Fig. 3, the strip can produce two surfaces that are bounded by edge(s). When the two short sides are identied with or without a half twist, the result is the Mobius strip (M2) or the cylindrical strip (C2), respectively. The latter has two edges, two faces and is orientable, as the normal to each face is uniquely dened at each point. The former has only one face and one edge and is non-orientable, as discussed above. The strip can also produce surfaces without edges. When, instead of gluing only two of the edges, all four edges are identied pairwise, the product is one of three compact, two-dimensional manifolds: the torus T2 (opposite edges glued without a twist), the Klein bottle K2 (one opposite pair glued with, one without, a half-twist), and the projective plane P2 (each pair of opposite edges glued with a half twist). T2 is orientable, but K2 and P2 are not. All three are edgeless.

Fig. 4 Double-cover relationship between a centro-symmetric cylindrical surface and a Mobius band. Two copies of the Mobius band glued appropriately yield a cylinder. In the process, the one marked point becomes two, whose relationship is one of inversion for a cylindrical strip embedded in 3D space.

on the vertices i. Now consider the map G(X2). If the surface X2 is a double cover of Y2, then a centrosymmetric map G(X2) with vX vertices is transformed into a map G1/2(Y2) with vY vX/2 vertices by the same operation of collapsing points that sends X2 to Y2. Each eigenvector of A(G) obeys a local condition lA cl i

vX X j1

Aij cl ; j

The property of M2 that will be useful in the present application is that of the double-cover relationship. If we can construct a surface Y2 by identifying pairs of points in a surface X2, i.e. collapsing each pair to a single point, then we say that X2 is a double cover of Y2. Now, every non-orientable surface has an orientable double cover,17 and in the case of the surfaces derived from the rectangular strip, the relationships are S2 ! P2, T2 ! K2 and C2 ! M2, where the arrow denotes collapses under the operation of identication of antipodal points . Thus, a sphere in which each pair of antipodal points is treated as a single point in the new space yields the projective plane, a centrosymmetric torus in which the same identication is made yields a Klein bottle, and a centrosymmetric cylindrical strip under the same transformation yields a Mobius band.17 The last of these cases is shown in Fig. 4, where it can be seen that each point of M2 corresponds to a pair of points in C2. This property of the surfaces translates readily into a property of graphs embedded in them. A graph G embedded in a surface S is a map, G(S). The adjacency spectrum of a graph is the set of eigenvalues {lA} found by diagonalising the matrix A(G) that has elements Aij 1 for vertices i and j joined by an edge of G and Aij 0 otherwise. Suppose that we have found a complete set of eigenvectors |lAi, with coecients {cl } dened i

j

where now j runs only over neighbours of i in G(X2). From this it is easy to see that every gerade eigenvector |lAi of A(G) gives an eigenvector of A(G1/2) with the same eigenvalue. As the centre of inversion lies outside the surface X2 ( C2, T2 or S2), the set of eigenvectors of Y2 can be symmetrised to yield equal numbers of gerade and ungerade vectors. Thus, the spectrum of A(G1/2) is exactly the gerade half of the spectrum of A(G). What is the signicance of the remaining ungerade half of the spectrum of A(G)? This becomes apparent from inspection of an example. Fig. 5 shows a graph (actually a simple cycle) drawn on C2, with the two types of eigenvector, and illustrates the fate of both graph and vectors on collapsing C2 to M2. The gerade vector collapses to an eigenvector of A(G1/2), as we have seen, obeying lA cl i

vY X j1

Aij G1=2 cl : j

The ungerade vector collapses to an eigenvector, not of A(G1/ 2), but of a matrix B(G1/2), say, which has the same entries as A(G1/2) except for those pairs of vertices joined by edges that run across the seam where the two ends of the rectangular region have been glued with a half twist. If Bij 1 is assigned to these edges, and Bij +1 to all others, then the Phys. Chem. Chem. Phys., 2002, 4, 28782883 2879

Fig. 5 Double-cover relationships for eigenvectors of graphs G(X2) and G1/2(Y2). In this case, X2 (left) is C2 and Y2 (right) is M2. (a) The centrosymmetric parent graph is a cyclic chain of 8 vertices, each vertex i having an antipodal image i0 , and G1/2 is a cycle of 4 vertices. If primes are ignored, each vertex has the same environment in G and G1/2 . (b) A gerade eigenvector of A(G) with equal coecients (a,b,...) on i and i0 , collapsed to a vector on G1/2 in which each coecient appears only once, with thesame neighbours as in G, and hence the same eigenvalue. (c) In an ungerade eigenvector of A(G), where coecients on i and i0 are equal and opposite, the neighbourhoods and eigenvalue are preserved only if the edge that crosses the seam of M2 (shown dotted) is taken with weight 1 in G1/2 . The collapsed vector is then an eigenvector, not of A(G1/2) but of B(G1/2), which turns out to be the Huckel Hamiltonian H(G1/2).

The spectral embedding result can therefore be restated in more chemical terms for the present case, as: If G1/2 is the Mobius graph obtained by collapsing antipodal vertices of the cylindrical graph G, then the Huckel p spectrum of G1/2 is the ungerade half and the Huckel s spectrum of G1/2 is the gerade half of the Huckel p spectrum of G. In the rest of the paper, the implications of this statement are explored for chemical examples. A similar result has been noted for polyhex graphs on the torus and Klein bottle, and fullerene graphs on the sphere and projective plane,19 and in fact it applies to general pairs G, G1/2 on these surfaces. The Mobius strip is potentially a much more signicant case for chemistry as, unlike K2 and P2, M2 can be constructed in 3D space without self-intersection.

4. Chemical examples

(i) Monocyclic rings The solution to the Huckel problem is well known for both types of monocyclic ring system (Huckel and Mobius) and can be found in many textbooks of pictorial molecular-orbital theory. A simple cycle Cn of n vertices j 1, 2,...n has Huckel energies ek a + lA b where lA is an eigenvalue of the adjak k cency matrix, lA C k 2 cos2kp=n k 6

collapsed vector clearly obeys the local eigenvalue condition eqn. (3) but with A substituted by B. Thus, the spectrum of the adjacency matrix of the graph G on the double cover splits exactly into the spectra of the matrices A(G1/2) and B(G1/2) for the graph G1/2 on the derived surface. The chemical signicance of this mathematical fact is that B is none other than the Huckel matrix for a p system on a non orientable surface. If we imagine attaching a set of perpendicular p orbitals to the vertices of a graph drawn on the rectangular strip, then the process of gluing with a half twist forces a phase dislocation in each of the bonds that crosses the seam (Fig. 6). In general, for a non-orientable surface the Hamiltonian matrix for a p system with Coulomb parameter a and bond parameter b is therefore H a1 bB 4

with the angular-momentum quantum number taking integral values of k 0; 1; 2; :::; n 1=2 n=2 odd n even n 7

whereas for a orientable surface (or for a s system on a nonorientable surface) it is the conventional H a1 bA 5

the degeneracy being 2 for all levels except those with k 0 and (for even n) k n/2. The (unnormalised) eigenvectors in real form have coecient on vertex j sin k; cj 2jkjpj=n; 8 cos with cosine solutions for all k and sine solutions only where the eigenvalue is doubly degenerate. The eigenvalue solution is enshrined in the mnemonic known as the Frost (or FrostMusulin) circle:20 draw a circle of radius 2 and inscribe the n-gon, point downwards, in the circle. The height, measured downwards from the centre, of each place where the polygon touches the circle is an allowed value of lA (Fig. 7). k For a Mobius cycle Mn of n atoms, the adjacency matrix has entries Aj; j1 Aj1; j 1 and An;1 A1;n 1 10 j 1; :::; n 1 9

involving the usual adjacency matrix. Eqn. (4) agrees with the practice for monocyclic Mobius graphs, introduced by Zim mermann,6 of calculating p energies by introducing a signreversed bond parameter for one of the bonds (see also ref. 18). If a is taken as the origin and |b| the unit of the energy scale, Huckel molecular orbital energies are simply the eigen values {lA} and {lB} in the two cases.

for the nal link in the cycle. The Huckel matrix in the reduced units has the same (j,j 1) elements, but H n;1 H 1;n 1

A H

11

The two sets of eigenvalues {l } and {l } are dened by functions of even and odd multiples of (p/n), respectively: lA Mn 2 cos 2kp=n; 2k 0; 2; 4; :::; n 1 n odd k or n n even

Fig. 6 Formation of a p system with Mobius topology introduces phase dislocation across the gluing seam.

12

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constructions have been given for the eigenvectors.22 The double-cover approach gives a rationalisation for the construction, shows how to determine the full set of accompanying eigenvectors, and suggests generalisations to all centrosymmetric cylindrical graphs and their Mobius derivatives. The double-cover geometrical construction also rationalises the observation that, for odd n, the adjacency and Huckel spectra of Mn are exactly inverted, i.e. flA M n g flH M n g; n odd 16

This follows easily from the CoulsonRushbrooke theorem23 for bipartite (alternant) p systems. In a bipartite graph, the vertices fall into two disjoint sets ( starred and unstarred ) such that all edges of the graph join a starred to an unstarred vertex. The theorem states that in a bipartite system each eigenvalue lA is matched by an eigenvalue lA, with eigenvector | lAi derived from |lAi by reversing the signs of coecients on all vertices of one set, say the starred vertices. The monocycle C2n is bipartite, and the starred and unstarred sets are exchanged by a rotation through (p/n) when n is even, but by the inversion operation when n is odd. Thus when n is odd, each g vector |lA(C2n)i has a u partner | lA(C2n)i, and this relationship is passed down to the spectra of Mn , proving eqn. (15). Such inversions also apply to a wider class of nonplanar bipartite graphs.19 The pairing theorem is discussed in the context of Mobius systems in refs. 24 and 25.

(ii)

Fig. 7 FrostMusulin circle constructions for spectra of simple and Mobius monocycles, Cn and Mn (n 4). (a) Adjacency spectrum of C4 and M4 ; (b) Huckel spectrum of M4 ; (c) unied construction of both spectra of M4 from the adjacency spectrum of the double cover (C8) by grouping alternate vertices into 4-cycles.

In-plane p systems

lH Mn 2 cos 2k1p=n; k 2k 1 1; 3; 5; :::; n 1 n even or n n odd 13 with corresponding sinusoidal eigenvectors eqn. (8), and degeneracies equal to 2 except when 2k 0, 2k n or 2k + 1 n. For odd cycles, these expressions lead to an exact inversion between adjacency and Mobius spectra. The Frost circle construction is easily adapted to the Mobius case: the adjacency eigenvalues are predicted when the n-gon is placed point down, the Huckel eigenvalues when the n-gon is placed with a horizontal edge lying lowest (Fig. 7b). In this form, the construction is known as the Zimmermann diagram. Thus the general relationship between monocycle spectra is, in a notation based on sets, flA M n g flA C n g; and flH M n g flA C 2n g flA C n g; 15 14

Mobius topology can also be encountered in conventional, untwisted cyclic systems. The in-plane tangential p orbitals of a monocycle of carbon or metal atoms may be used to construct delocalised molecular orbitals in much the same way as the out-of-plane tangential ( p ) orbitals.26,27 When the number of atoms in the cycle is odd, at least one phase interruption must be present in the tangential system, and the manifold of energy levels is, apart from any re-scaling of the b integral, exactly that of the p Huckel matrix of a Mobius cycle, {lH(Mn)}; when the number is even, the tangential manifold is that of the Huckel system of the untwisted cycle, {lH(Cn)} (see Fig. 8). Thus for in and out p systems (i.e. in-plane and out-ofplane, respectively), the spectra are related as flout C n g flA C n g all n 17

which is given a direct geometrical interpretation by a combined Frost circle (Fig. 7c). To nd both spectra of a Mobius monocycle Mn , inscribe a 2n-gon in the circle, point down; then, beginning with the bottom point, assign every second contact between polygon and circle to the adjacency spectrum of Mn and Cn (black dots in the gure); the remaining n points of contact dene the Huckel spectrum of Mn (unlled circles in the gure). The two diagrams, often presented in separate courses of an undergraduate chemistry curriculum, are actually halves of a single whole. The double-circle device itself has been proposed in the literature before,21 and partial

Fig. 8 Equivalence of in-plane p systems to Mobius and untwisted out-of-plane p systems for (a) odd and (b) even monocycles. In each case are shown, from left to right, the basis, Hamiltonian matrix, energy-level diagram and eigenvectors.

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flA Mn g

21

flH Mn g

and the Frost-circle construction of Fig. 7 can encapsulate both systems, with the two half-sets of vertices of a (4n + 2)gon indicating in- and out-of-plane p energies of a (2n + 1)atom cycle, and the whole set of vertices of a 2n-gon the in- and out-of-plane p levels for a 2n-atomic cycle. As eqn. (18) shows, for odd cycles, the in- and out-of-plane orbital energies, in units of the appropriate |b|, are exact inversions of each other, for the reasons discussed earlier in connection with eqn. (15). (iii) Cyclic polyacenes

22

where j 1,...n in each case. The bi-partite spectrum {lA(C[2n])} is split between adjacency and Hamiltonian spectra of M[n] : if an eigenvalue l belongs to {lA(M[n])}, then l belongs to {lH(M[2n])}. The pair of zero eigenvalues in {lA(C[2n])} is split between {lA(M[n])} and {lH(M[2n])}. Symbolically, flA M n g flH M n g and flA C 2n g flA M n g flH M n g 24 23

The cyclic polyacenes are hypothetical cylindrical molecules resulting formally from the closure of a linear polyacene by annelation of its end rings. The Huckel spectrum of the cyclic polyacene on n benzene rings, C[n] , is pi 1h 20 flA Cn g a b 9 8 cos 2pk=n 2 where a and b independently take values 1, and k runs from 1 to n.2830 The bonding levels all have b +1, and for even n there are two zero eigenvalues (a +1, b + 1, k n/2 and (a 1, b 1, k n/2). When the number of benzene rings is even, the cyclic polyacene is centrosymmetric. Parity labels g and u are assigned as follows: (a +1, b + 1, parity g/u as k is even/odd), (a 1, b + 1, parity u/g as k is even/ odd), g/u labels reverse under the double sign change (a, b) ! (a, b). The spectra for the Mobius polyacene, M[n] , follow from the double-cover relationship with C[2n] . The 4n eigenvalues for the adjacency and Hamiltonian matrices are respectively

An example of the relationship between the three spectra is shown for n 5 in Fig. 9.

5. Conclusion

A topological relationship between two surfaces, the cylinder and the Mobius band has been shown to lead to a simple gen eral relationship betwen the spectra of cylindrical and Mobius graphs. For any graph drawn on the Mobius strip, the spectra of its adjacency and Huckel matrices span the disjoint gerade and ungerade halves of the adjacency spectrum of the cylindrical double-cover graph. This gives a simple decription of pure p systems on the Mobius band; in real chemical systems sp interaction is likely to be an additional complicating eect,11,12 and the twist, which is free to move in the idealised non-orientable mathematical band, may become localised and locked into a xed C2 symmetry in a chemical realisation.13 Eigenvalue properties and their consequences for electronic structure have been emphasised here. Eigenvectors serve as models for molecular orbitals but they can also be used to estimate coordinates for embedding molecular frameworks in 3D space. The double-cover relationship suggests a useful trick for obtaining starting coordinates of a Mobius graph G1/2 : deter mine topological coordinates for G on the cylinder in the usual way,31 take one half of the cylindrical surface and twist it onto the Mobius band of unit radius parameterised as e.g.32 fx; y; zg fcosu1 v cosu=2; sinu1 v cosu=2; v sinu=2g 25 for 0 p u p 2p, |v| p vmax . This circumvents diculties of identifying the p-orbital-like eigenvectors directly for G1/2 .

References

1 2 3 Fig. 9 Spectral relations of cylindrical and Mobius polyacenes: the adjacency spectrum of the centrosymmetric cylindrical polyacene with 10 hexagonal rings (left) includes both the adjacency (centre) and Hamiltonian (right) spectra of the derived Mobius system with 5 hex agonal rings. 4 5 6 The New Journal of Chemistry, ed. J. P. Sauvage, October/ November issue of vol. 17, 1993. D. B. Amabilino, P. R. Ashton, A. S. Reder, N. Spencer and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1994, 33, 1286. Chemical Topology: Applications and Techniques, ed. D. Bonchev and D. H. Rouvray, vol. 6 of Mathematical Chemistry, Gordon & Breach, Amsterdam, 2000. E. Flapan, When Topology Meets Chemistry, Cambridge University Press, 2000. E. Heilbronner, Tetrahedron Lett., 1964, 5, 1923. H. E. Zimmermann, J. Am. Chem. Soc., 1966, 88, 1564.

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7 S. Martin-Santamaria, B. Lavan and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2, 2000, 1415. 8 D. M. Walba, R. M. Richards and R. C. Haltiwanger, J. Am. Chem. Soc., 1982, 104, 3219. 9 L. Turker, Turk. J. Chem., 1997, 21, 415. 10 L. Turker, J. Mol. Struct. (THEOCHEM), 1998, 454, 83. 11 S. Martin-Santamaria, B. Lavan and H. S. Rzepa, J. Chem. Soc., Chem. Commun., 2000, 1089. 12 S. Martin-Santamaria and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2, 2000, 2372. 13 S. Martin-Santamaria and H. S. Rzepa, J. Chem. Soc., Perkin Trans. 2, 2000, 2378. 14 S. Barr, Experiments in Topology, Dover Publications Inc., New York, 1989. 15 J. Stillwell, Geometry of Surfaces, Springer, New York, 1992. 16 F. Klein, Math. Ann., 1876, 9, 476. 17 J. Stillwell, Classical Topology and Combinatorial Group Theory, Springer, New York, 2nd edn., 1993. 18 I. Gutman, Z. Naturforsch. A, 1978, 33, 214. 19 M. Deza, P. W. Fowler, A. Rassat and K. M. Rogers, J. Chem. Inf. Comput. Sci., 2000, 40, 550.

20 A. A. Frost and B. Musulin, J. Chem. Phys., 1953, 21, 572. 21 U. Norinder, O. Wennerstrom and H. Wennerstrom, Tetrahedron Lett., 1984, 25, 1937. 22 R. F. Langler, G. Salgado and C. Mendizabal, Quim. Nova, 2000, 23, 841. 23 C. A. Coulson and G. S. Rushbrooke, Proc. Camb. Philos. Soc,, 1940, 36, 193. 24 I. Gutman, R. B. Mallion and D. H. Rouvray, J. Math. Chem., 1991, 8, 355. 25 Z. Zhou, Int. J. Quantum Chem., 1994, 51, 181. 26 T. A. Albright, J. K. Burdett, M. H. Whangbo, Orbital Interactions in Chemistry, Wiley, NY, 1985, pp. 7273. 27 D. M. P. Mingos and D. J. Wales, Introduction to Cluster Chemistry, Prentice-Hall, Englewood Clis, NJ, 1990, p. 139. 28 I. Gutman, Commun. Math. Chem., 1980, 8, 291. 29 I. Gutman, P. U. Biedermann, V. Ivanov-Petrovic and I. Agranat, Polycyclic Aromat. Compd., 1996, 8, 189. 30 I. Gutman, Polycyclic Aromat. Compd., 1996, 8, 251. 31 D. E. Manolopoulos and P. W. Fowler, J. Chem. Phys., 1992, 96, 7603. 32 A. Gray and S. Krantz, Modern Dierential Geometry of Curves and Surfaces, CRC Press, Boca Raton, 1993.

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